4-(Trifluoromethoxy)benzylamine → Ethyl 5-methyl-2-[4-(trifluoromethoxy)phenyl]-1H-imidazole-4-carboxylate

HRID 229854Notes

Reaction equation

HRID 229854 reaction equation
[N:1](=[C:3]([C:9]([CH3:11])=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])O.[F:12][C:13]([F:24])([F:23])[O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1>C(#N)C>[CH2:7]([O:6][C:4]([C:3]1[N:1]=[C:19]([C:18]2[CH:21]=[CH:22][C:15]([O:14][C:13]([F:12])([F:23])[F:24])=[CH:16][CH:17]=2)[NH:20][C:9]=1[CH3:11])=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 178472877HCID 178472877, compound

Product 1

HCID 53404402Ethyl 5-methyl-2-[4-(trifluoromethoxy)phenyl]-1H-imidazole-4-carboxylateYield 71.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7.9 g of ethyl 2-oximinoacetoacetate in acetonitrile (100 ml) was added 10.5 g of 4-(trifluoromethoxy)benzylamine (as R4—CH2—NH2). The reaction mixture was then refluxed for 17 hours under argon atmosphere. After such time the reaction mixture was cooled down to 0° C., the solid was filtered off, washed with acetonitrile, and dried in vacuo to yield 11.2 g of a light yellow powder, MS (ISP) 315 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then refluxed for 17 hours under argon atmosphere
  2. filtrationthe solid was filtered off
  3. washwashed with acetonitrile
  4. customdried in vacuo

Sources & evidence

ORD record
ord-887971a452514cba90cd6752ffff4cf7
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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