Ammonia → 3-(4-Methyl-imidazol-1-yl)-5-trifluoromethyl-benzamide

HRID 1678349Notes

Reaction equation

HRID 1678349 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[C:9]([C:15]([F:18])([F:17])[F:16])[CH:10]=[C:11]([CH:14]=2)[C:12]#[N:13])[CH:6]=1.N.[OH:20]O.O>CN1C(=O)CCC1>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:14]=[C:11]([CH:10]=[C:9]([C:15]([F:18])([F:16])[F:17])[CH:8]=2)[C:12]([NH2:13])=[O:20])[CH:6]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 962WaterHCID 469003933-(4-Methyl-1H-imidazol-1-YL)-5-(trifluoromethyl)benzonitrile

Product 1

HCID 594312843-(4-Methyl-imidazol-1-yl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 5-(4-methyl-imidazol-1-yl)-3-trifluoromethyl-benzonitril (3.5 g, 13.93 mmol) in NMP (28 mL) is treated with aqueous ammonia (9.8 mL, 25%) and aqueous hydrogen peroxide (3.5 mL, 30%). The resulting mixture is stirred for 1 hour at 20-25° C. and then poured into chilled water (420 mL). The resulting suspension is filtered and the filter cake is washed with water (50 mL), and dried in vacuo at 50° C. to give 3.2 g of the title compound (XXIII) (85.4%) as white crystals (98% area by HPLC).

Workup

  1. additionpoured
  2. filtrationThe resulting suspension is filtered
  3. washthe filter cake is washed with water (50 mL)
  4. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-549970c5295e434583f8e8c1088ddc6d
Source dataset
uspto-grants-2011_08
Patent number
US08008504B2

Reaction notes

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