3-(Trifluoromethyl)benzoyl chloride → HCID 20085589, compound

HRID 1608823Notes

Reaction equation

HRID 1608823 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:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([Cl:25])=[O:24]>>[ClH:25].[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:23](=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=1

Participants

3

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085589HCID 20085589, compoundYield 85.5%

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 11 using 14.1 g (0.0612 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl]benzamide, prepared as in Example 6A, and 25.5 g (0.1224 mol) of m-trifluoromethylbenzoyl chloride with the exception that after removing ethyl acetate the resulting solid was suspended in methanol. To this suspension was added a diethyl ether/hydrochloric acid solution. The resulting solution was reduced to dryness under reduced pressure and the final product was recrystallized from an ethanol/diethyl ether solution to provide 22.97 g of the desired titled compound (m.p. 199°-201.5° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. customthat after removing ethyl acetate the resulting solid
  3. additionTo this suspension was added a diethyl ether/hydrochloric acid solution
  4. customthe final product was recrystallized from an ethanol/diethyl ether solution

Sources & evidence

ORD record
ord-5899951a6cd445359d1019453d3cb424
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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