4-Isopropylbenzoyl chloride → HCID 20085556, compound

HRID 1608824Notes

Reaction equation

HRID 1608824 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].[CH:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([Cl:27])=[O:26])=[CH:23][CH:22]=1)([CH3:20])[CH3:19]>>[ClH:27].[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:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([CH:18]([CH3:19])[CH3:20])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 27594864-Isopropylbenzoyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085556HCID 20085556, compound

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 11 using 2.50 g (0.0109 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl]benzamide, prepared as in Example 6A, and 4.0 g (0.0217 mol) of p-isopropylbenzoyl chloride with the exception that, after removing ethyl acetate the resulting solid was purified using column chromatography (8000 ml of a gradient eluent of 0-15% methanol in a 1% ammonia in dichloromethane solution). The fractions containing the desired product were combined and reduced to dryness under reduced pressure to provide 2.1 g of a solid. This solid was then dissolved in methanol containing diethyl ether and hydrochloric acid and the resulting solution was again reduced to dryness under reduced pressure. The final product was recrystallized from an ethanol/diethyl ether solution to provide 2.37 g of the desired titled compound (m.p. 188°-192° C.).

Workup

  1. customafter removing ethyl acetate the resulting solid
  2. customwas purified
  3. additionThe fractions containing the desired product

Sources & evidence

ORD record
ord-5f4a75ec088a4a998d0fff9eec8c44a3
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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