Acetic Acid → HCID 178448762, compound
Reaction equation
ClC[C:3]([CH3:9])([CH3:8])[C:4](C#N)=O.Br.O.[NH2:12][NH:13][C:14]([NH:16][NH2:17])=[S:15].[ClH:18].[C:19]([OH:22])(=O)[CH3:20]>>[NH2:12][N:13]1[C:19](=[O:22])[CH:20]([Cl:18])[N:17]([C:3]([CH3:4])([CH3:8])[CH3:9])[N:16]=[C:14]1[SH:15]Participants
Procedure
2.31 kg (15.88 moles) of chloropivaloyl cyanide were added to 9 liters of a solution of hydrogen bromide in glacial acetic acid (33% strength) at room temperature, while stirring. The mixture was subsequently stirred at room temperature for 4 hours. 288 ml (15.88 moles) of water were then added at 7° to 10° C. (exothermic reaction, about 37° C.) and the mixture was subsequently stirred at room temperature for 3 hours. Thereafter, the reaction solution was introduced into a mixture of 2.03 kg of thiocarbohydrazide and 15.9 liters of 1 N hydrochloric acid at 7° to 10° C. (highly exothermic reaction). This reaction mixture was subsequently stirred at 7° to 10° C. for 2 hours and at room temperature for 14 hours. Thereafter, the crystals which had precipitated were filtered off, washed with water and dried. 2,995 g (80.4% of theory) of crude 4-amino-6 -chloro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one of melting point 202°-208° C. were obtained.
Workup
- stirringThe mixture was subsequently stirred at room temperature for 4 hours
- custom(exothermic reaction, about 37° C.)
- stirringthe mixture was subsequently stirred at room temperature for 3 hours
- customhighly exothermic reaction)
- stirringThis reaction mixture was subsequently stirred at 7° to 10° C. for 2 hours and at room temperature for 14 hours
- customThereafter, the crystals which had precipitated
- filtrationwere filtered off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-92c987afd86c41e3b48cc51b4addb1ab
- Source dataset
- uspto-grants-1983_06
- Patent number
- US04386953
Reaction notes
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