US4013649A
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Method of making 4-amino-6-t-butyl-3-mercapto-1,2,4-triazin-5-one
Assignee: EIDP Inc
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Filing: 1974-10-11
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Granted: 1977-03-22
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Expires: 1994-10-11
Abstract
Abstract Method of making 4-amino-6-t-butyl-3-mercapto-1,2,4-triazin-5-one comprising halogenating a 3,3-dimethylbutyric acid with Br 2 or Cl 2 to produce a 2,2-dihalo-3,3-dimethylbutyric acid then reacting the latter with thiocarbohydrazide. Alternatively, a 3,3-dimethylbutyryl chloride can be used as starting material, in which case the halogenation product is contacted with water, an aqueous base, an alcohol, a mercaptan, or an amine to convert it to an acid or salt thereof, anhydride, ester, thioester or amide, and the latter is reacted with thiocarbohydrazide.
Inventors
- 👤 Mitchell Joseph Bogdanowicz, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 10:28
CPC Classifications
C; C07; C07C; C07C53/00; C07C53/15; C07C53/19; C07D; C07D253/00; C07D253/02; C07D253/06
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
169 words
A method of making 4-amino-6-t-butyl-3-mercapto-1,2,4-triazin-5-one which comprises: a. reacting a compound of the formula: ##EQU10## where R is H, Br or Cl and Y is Cl, Br or OH; with Br 2 or Cl 2 , in the presence of a catalyst when Y is OH, to produce a compound of the formula: ##EQU11## where X and Z are each independently Cl or Br and Y' is Cl or Br; then, contacting the compound with a compound selected from R 1 OH, R 1 SH and R 2 R 3 NH, where R 1 is H, C 1 -C 4 alkyl, phenyl, benzyl, an alkali metal cation, or an alkaline earth metal cation, and R 2 and R 3 are each independently H, C 1 -C 4 alkyl, phenyl or benzyl; to form a compound of the formula: ##EQU12## where Q is --OR 1 , --SR 1 , --NR 2 R 3 or ##EQU13## then b. reacting the product of step a. with thiocarbohydrazide in a polar inert solvent.
Claim 2
Independent Claim
169 words
A method of making 4-amino-6-t-butyl-3-mercapto-1,2,4-triazin-5-one which comprises: a. reacting a compound of the formula: ##EQU10## where R is H, Br or Cl and Y is Cl, Br or OH; with Br 2 or Cl 2 , in the presence of a catalyst when Y is OH, to produce a compound of the formula: ##EQU11## where X and Z are each independently Cl or Br and Y' is Cl or Br; then, contacting the compound with a compound selected from R 1 OH, R 1 SH and R 2 R 3 NH, where R 1 is H, C 1 -C 4 alkyl, phenyl, benzyl, an alkali metal cation, or an alkaline earth metal cation, and R 2 and R 3 are each independently H, C 1 -C 4 alkyl, phenyl or benzyl; to form a compound of the formula: ##EQU12## where Q is --OR 1 , --SR 1 , --NR 2 R 3 or ##EQU13## then b. reacting the product of step a. with thiocarbohydrazide in a polar inert solvent.
Claim 3
Dependent Claim
63 words
Method of claim 1 wherein step a. is carried out at 75° - 200°C. and 1 - 20 atmospheres and the catalyst, when Y is OH, is selected from phosphorus and its halides, oxyhalides, oxygen acids and oxides, thionyl chloride, phosgene, 3,3-dimethylbutyryl chloride, 2-halo- and 2,2-dihalo-3,3-dimethylbutyryl halide, and wherein step b. is carried out at 20° - 160°C. and 1 - 5 atmospheres.
Claim 4
Dependent Claim
38 words
Method of claim 2 wherein step a. is carried out at 150° - 170°C. and 1 - 5 atmospheres and step b. is carried out at 1 - 2 atmospheres and 50° - 100°C. in a water/alcohol medium.
Claim 5
Dependent Claim
37 words
Method of claim 3 wherein the starting material is 3,3-dimethylbutyric acid, in step a. the halogen is Br 2 and the catalyst is PCl 3 , and step b. is carried out at 1 atmosphere in water/methanol.
Claim 6
Dependent Claim
66 words
Method of claim 1 wherein the starting material is 3,3-dimethylbutyryl chloride, step a. is carried out at 1 - 5 atmospheres and 0° - 50°C. in a tertiary organic amine solution, the reaction mixture is contacted with water to form the tertiary amine salt of the 2,2-dihalo-3,3-dimethylbutyric acid for use in step b. which is carried out at 20° - 160°C. and 1 - 5 atmospheres.
Claim 7
Dependent Claim
48 words
Method of claim 5 wherein in step a. the halogen is Br 2 , the tertiary amine is pyridine, the temperature is 5° - 15°C. and the pressure is 1 atmosphere and step b is carried out at 50° - 100°C. and 1 - 2 atmospheres in water/methanol.
Claim 8
Independent Claim
86 words
A method of making 4-amino-6-t-butyl-3-mercapto-1,2,4-triazon-5-one which comprises reacting a compound of the formula: ##EQU14## where X and Z are each independently Cl or Br and Q is --OR 1 , --SR 1 , --NR 2 R 3 or ##EQU15## where R 1 is H, C 1 -C 4 alkyl, phenyl, benzyl, an alkali metal cation, or an alkaline earth metal cation, and R 2 and R 3 are each independently H, C 1 -C 4 alkyl, phenyl or benzyl; with thiocarbohydrazide in a polar inert solvent.
Claim 9
Independent Claim
86 words
A method of making 4-amino-6-t-butyl-3-mercapto-1,2,4-triazon-5-one which comprises reacting a compound of the formula: ##EQU14## where X and Z are each independently Cl or Br and Q is --OR 1 , --SR 1 , --NR 2 R 3 or ##EQU15## where R 1 is H, C 1 -C 4 alkyl, phenyl, benzyl, an alkali metal cation, or an alkaline earth metal cation, and R 2 and R 3 are each independently H, C 1 -C 4 alkyl, phenyl or benzyl; with thiocarbohydrazide in a polar inert solvent.
Claim 10
Dependent Claim
17 words
Method of claim 7 wherein the reaction is carried out at 20° - 160°C and 1-5 atmospheres.
Claim 11
Dependent Claim
19 words
Method of claim 8 wherein the reaction is carried out at 50°-160°C and 1-2 atmospheres in a water/alcohol medium.
References Cited (Backward Citations)
US3544570A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-21 | 1980-09-20 | 1981-03-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-21 | 1984-09-20 | 1985-03-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-21 | 1988-09-20 | 1989-03-22 | $7700.00 | Window Closed / Lapsed |