Ammonia → HCID 66958665, compound

HRID 2283895Notes

Reaction equation

HRID 2283895 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])=[CH:8][C:7]([C:15]([O:17]CC)=O)=[N:6]1)[CH2:2][CH2:3][CH3:4].[NH3:20]>CO>[CH2:1]([N:5]1[C:9]([CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])=[CH:8][C:7]([C:15]([NH2:20])=[O:17])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66958407HCID 66958407, compound

Product 1

HCID 66958665HCID 66958665, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 1-butyl-5-(2-hydroxy-2-methylpropyl)-1H-pyrazole-3-carboxylate (26 g, 97 mmol) and ammonia (160 mL of a 7 N solution in methanol) were heated at 150° C. in a stainless steel reactor for 42 hours and allowed to cool to ambient temperature. The volatiles were removed under reduced pressure to provide 1-butyl-5-(2-hydroxy-2-methylpropyl)-1H-pyrazole-3-carboxamide as a black oil, which was treated with trifluoroacetic anhydride (40 mL, 289 mmol) and triethylamine (53 mL, 386 mmol) according to a modification of the method of Part C of Example 1253 to provide 2-(1-butyl-3-cyano-1H-pyrazol-5-yl)-1,1-dimethylethyl trifluoroacetate as a dark brown oil. The reaction with trifluoroacetic anhydride was stirred for three hours.

Workup

  1. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-ba55deec36f54eb4b2982e7466097df9
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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