US3989698A
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Process for preparing benzoxazines
Assignee: PMC Inc
•
Filing: 1975-02-20
•
Granted: 1976-11-02
•
Expires: 1995-02-20
Abstract
Abstract This invention relates to a process for preparing benzoxazines and more particularly 2-substituted-4H-3,1-benzoxazine-4-ones, obtained by reacting at least at about room temperature in the presence of an effective amount of a tertiary amine an isatoic anhydride with an acylating compound consisting of either a carboxylic acid anhydride or an acyl halide.
Inventors
- 👤 Richard L. Jacobs
- 👤 Richard L. Hively
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 03:28
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/04; C07D265/12; C07D265/14; C07D265/20; C07D265/22; A; A01; A01N; A01N43/00; A01N43/72; A01N43/86; C07D239/00; C07D239/70; C07D239/72; C07D239/86; C07D239/88; C07D239/91; C07D239/92
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
77 words
A process for preparing benzoxazines which comprises reacting at temperatures of at least about 25° C in the presence of a catalytic amount of at least one tertiary amine, approximately stoichiometric amounts of an isatoic anhydride with an acylating compound selected from the class consisting of (a) carboxylic acid anhydrides and (b) acyl halides having the formulae ##EQU1## wherein X is halogen and R is a saturated or unsaturated organic radical having up to 30 carbon atoms.
Claim 2
Dependent Claim
77 words
A process for preparing benzoxazines which comprises reacting at temperatures of at least about 25° C in the presence of a catalytic amount of at least one tertiary amine, approximately stoichiometric amounts of an isatoic anhydride with an acylating compound selected from the class consisting of (a) carboxylic acid anhydrides and (b) acyl halides having the formulae ##EQU1## wherein X is halogen and R is a saturated or unsaturated organic radical having up to 30 carbon atoms.
Claim 3
Dependent Claim
31 words
The process of claim 1 further characterized in that R is a substituted or unsubstituted organic radical selected from the class consisting of alkyl, aryl, alkaryl, aralkyl, cycloalkyl, and heterocyclic radicals.
Claim 4
Dependent Claim
14 words
The process of claim 2 further characterized in that R is a substituted-organic radical.
Claim 5
Dependent Claim
31 words
The process of claim 1 further characterized in that the benzoxazine is 2-alkyl-4H-3,1-benzoxazine-4-one prepared by reacting the isatoic anhydride with an aliphatic carboxylic acid anhydride having up to 30 carbon atoms.
Claim 6
Dependent Claim
24 words
The process of claim 1 further characterized in that the benzoxazine is 2-alkyl-4H-3,1-benzoxazine-4-one prepared by reacting the isatoic anhydride with an aliphatic acyl chloride.
Claim 7
Dependent Claim
31 words
The process of claim 1 further characterized in that the benzoxazine is 2-aryl-4H-3,1-benzoxazine-4-one prepared by reacting the isatoic anhydride with an aromatic carboxylic acid anhydride having up to 30 carbon atoms.
Claim 8
Dependent Claim
24 words
The process of claim 1 further characterized in that the benzoxazine is 2-substituted-aryl-4H-3,1-benzoxazine-4-one prepared by reacting the isatoic anhydride with an aromatic acyl chloride.
Claim 9
Dependent Claim
13 words
The process of claim 1 further characterized in that the halogen is chlorine.
Claim 10
Dependent Claim
34 words
The process of claim 1 further characterized in that the tertiary amine comprises pyridine and is present in an amount ranging up to about ten times the amount by weight of the isatoic anhydride.
Claim 11
Dependent Claim
21 words
The process of claim 1 further characterized in that the reaction temperature ranges from about 25° C to about 125° C.
Claim 12
Dependent Claim
21 words
The process of claim 1 further characterized in that the isatoic anhydride is a substituted-isatoic anhydride having 0 to 4 substituents.
Claim 13
Dependent Claim
41 words
The process of claim 11 further characterized in that the substituted-isatoic anhydride has the formula ##SPC9## wherein R 1 is selected from the class consisting of hydrogen, halo, nitro, lower alkoxy, alkenyloxy or alkyl radical of 1 to 8 carbon atoms.
Claim 14
Dependent Claim
34 words
The process of claim 1 further characterized in that a 4H-3,1-benzoxazine-4-one is prepared by reacting about 1.0 mole of an isatoic anhydride with about 1.0 mole of a saturated or unsaturated carboxylic acid anhydride.
Claim 15
Dependent Claim
19 words
The process of claim 13 further characterized in that the carboxylic acid anhydride is an aliphatic carboxylic acid monoanhydride.
Claim 16
Dependent Claim
19 words
The process of claim 13 further characterized in that the carboxylic acid anhydride is an aromatic carboxylic acid monoanhydride.
Claim 17
Dependent Claim
15 words
The process of claim 14 further characterized in that the monoanhydride is acetic acid anhydride.
Claim 18
Dependent Claim
18 words
The process of claim 15 further characterized in that the aromatic carboxylic acid monoanhydride is a substituted-aromatic monoanhydride.
Claim 19
Dependent Claim
19 words
The process of claim 14 further characterized in that the carboxylic acid anhydride is a substituted-aliphatic carboxylic acid monoanhydride.
Claim 20
Dependent Claim
38 words
The process of claim 1 further characterized in that a di-4H-3,1-benzoxazine-4-one is prepared by reacting about 1.0 mole of an isatoic anhydride with about 1.0 mole of carboxylic acid anhydride in the presence of effective amounts of pyridine.
Claim 21
Dependent Claim
16 words
The process of claim 19 further characterized in that the carboxylic acid anhydride is acetic anhydride.
Claim 22
Dependent Claim
19 words
The process of claim 19 further characterized in that the carboxylic acid anhydride is a substituted-aromatic carboxylic acid anhydride.
Claim 23
Dependent Claim
49 words
The process of claim 13 further characterized in that the carboxylic acid anhydride has the formula ##STR22## wherein R is either a divalent or monovalent organic radical having up to 30 carbon atoms and is selected from the class consisting of alkyl, aryl, alkaryl, aralkyl, cycloalkyl and heterocyclic radicals.
Claim 24
Dependent Claim
13 words
The process of claim 22 further characterized in that R is styryl radical.
Claim 25
Dependent Claim
13 words
The process of claim 22 further characterized in that R is phenyl radical.
Claim 26
Dependent Claim
15 words
The process of claim 22 further characterized in that R is a halo-substituted phenyl radical.
Claim 27
Dependent Claim
15 words
The process of claim 22 further characterized in that R is an alkoxy-substituted phenyl radical.
Claim 28
Dependent Claim
14 words
The process of claim 22 further characterized in that R is nitro-substituted phenyl radical.
Claim 29
Dependent Claim
15 words
The process of claim 22 further characterized in that R is a halo-substituted alkyl radical.
Claim 30
Dependent Claim
15 words
The process of claim 28 further characterized in that the halo-substituted alkyl radical is chloromethyl.
Claim 31
Dependent Claim
17 words
The process of claim 25 further characterized in that the halo-substituted phenyl radical is chloro-substituted phenyl radical.
Claim 32
Dependent Claim
17 words
The process of claim 26 further characterized in that the alkoxy-substituted phenyl radical is methoxy-substituted phenyl radical.
Claim 33
Dependent Claim
67 words
The process of claim 1 further characterized in that 4H-3,1-benzoxazine-4-one is prepared by reacting about 1.0 mole of the isatoic anhydride with about 1.0 mole of the organic halide having the formula ##STR23## wherein X is a halogen and R is a substituted or unsubstituted organic radical having up to 30 carbon atoms selected from the class consisting of alkyl, aryl, alkaryl, aralkyl, cycloalkyl and heterocyclic radicals.
Claim 34
Dependent Claim
12 words
The process of claim 32 further characterized in that X is chlorine.
Claim 35
Dependent Claim
14 words
The process of claim 32 further characterized in that R is an alkyl radical.
Claim 36
Dependent Claim
14 words
The process of claim 32 further characterized in that R is an aryl radical.
Claim 37
Dependent Claim
14 words
The process of claim 32 further characterized in that R is a styryl radical.
Claim 38
Dependent Claim
14 words
The process of claim 32 further characterized in that R is a phenyl radical.
Claim 39
Dependent Claim
15 words
The process of claim 32 further characterized in that R is a halo-substituted phenyl radical.
Claim 40
Dependent Claim
15 words
The process of claim 38 further characterized in that the halo-substituted phenyl radical is chlorophenyl.
Claim 41
Dependent Claim
15 words
The process of claim 32 further characterized in that R is an alkoxy-substituted phenyl radical.
Claim 42
Dependent Claim
15 words
The process of claim 40 further characterized in that the alkoxy-substituted phenyl radical is methoxyphenyl.
Claim 43
Dependent Claim
15 words
The process of claim 32 further characterized in that R is a nitro-substituted phenyl radical.
Claim 44
Dependent Claim
15 words
The process of claim 32 further characterized in that R is a halo-substituted alkyl radical.
Claim 45
Dependent Claim
15 words
The process of claim 43 further characterized in that the halo-substituted alkyl radical is chloromethyl.
Claim 46
Dependent Claim
13 words
The process of claim 32 further characterized in that R is furfuryl radical.
Claim 47
Dependent Claim
14 words
The process of claim 22 further characterized in that R is a furfuryl radical.
Claim 48
Dependent Claim
43 words
The process of claim 1 further characterized in that the substituted isatoic anhydride has the formula ##SPC10## wherein R 1 is selected from the class consisting of hydrogen, halo, nitro, lower alkoxy, lower alkenyloxy and alkyl radical of 1 to 8 carbon atoms.
Claim 49
Dependent Claim
38 words
The process of claim 1 further characterized in that a 4H-3,1-benzoxazine-4-one is prepared by reacting about 1.0 mole of an isatoic anhydride with about 1.0 mole of an acyl halide having the formula ##STR24## wherein X is chlorine.
Claim 50
Dependent Claim
37 words
The process of claim 1 further characterized in that a bis-4H-3,1-benzoxazine-4-one is prepared by reacting about 2.0 moles of an isatoic anhydride with 1.0 mole of an acyl halide having the formula ##STR25## wherein X is chlorine.
Claim 51
Dependent Claim
37 words
The process of claim 1 further characterized in that a di-4H-3,1-benzoxazine-4-one is prepared by reacting about 2.0 moles of an isatoic anhydride with 1.0 mole of an acyl halide having the formula ##STR26## wherein X is chlorine.
References Cited (Backward Citations)
US3531509A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-02 | 1980-05-03 | 1980-11-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-02 | 1984-05-03 | 1984-11-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-02 | 1988-05-03 | 1988-11-02 | $7700.00 | Window Closed / Lapsed |