4-Phenylbenzoyl chloride → N-[2-(1H-Imidazol-2-yl)ethyl]-2-[[4-phenylbenzoyl]amino]-benzamide

HRID 1608822Notes

Reaction equation

HRID 1608822 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].[C:18]1([C:24]2[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[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:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 841514-Phenylbenzoyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085661N-[2-(1H-Imidazol-2-yl)ethyl]-2-[[4-phenylbenzoyl]amino]-benzamideYield 65.1%

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 11 using 1.50 g (0.00651 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide, prepared as in Example 6A, and 3.76 g (0.01738 mol) of p-phenylbenzoyl chloride, with the exception that after removing ethyl acetate the final product was recrystallized from an ethyl acetate/methanol solution to provide 1.74 g of the desired titled compound (m.p. 197°-201° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. customthat after removing ethyl acetate the final product
  3. customwas recrystallized from an ethyl acetate/methanol solution

Sources & evidence

ORD record
ord-b49cd440b06c417ea0ab2a0218cc8d56
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

Loading…