4-(Trifluoromethyl)benzoyl chloride → N-[2-(1H-Imidazol-2-yl)ethyl]-2-[[4-(trifluoromethyl)-benzoyl]amino]benzamide

HRID 1608827Notes

Reaction equation

HRID 1608827 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)=[O:5].[F:18][C:19]([F:30])([F:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>C(OCC)(=O)C>[NH:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[NH:1][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([C:19]([F:18])([F:29])[F:30])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085692N-[2-(1H-Imidazol-2-yl)ethyl]-2-[[4-(trifluoromethyl)-benzoyl]amino]benzamideYield 85.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 11 using 2.00 g (0.00869 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl]benzamide, prepared as in Example 6A, and 3.62 g (0.01738 mol) of p-trifluoromethylbenzoyl chloride with the exception that removal of ethyl acetate provided a solid. This solid was recrystallized from ethyl acetate containing a small amount of methanol to provide 3.00 g of the desired titled compound (m.p. 207°-215° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. customprovided a solid
  3. customThis solid was recrystallized from ethyl acetate containing a small amount of methanol

Sources & evidence

ORD record
ord-e4c2ab607abe45e18466599201fa5356
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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