4-Chloroaniline → HCID 20432347, compound

HRID 2412482Notes

Reaction equation

HRID 2412482 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[N:7]=[C:8]([F:30])[N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)([OH:3])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[Cl:46][C:47]1[CH:53]=[CH:52][C:50]([NH2:51])=[CH:49][CH:48]=1>C(Cl)Cl>[Cl:46][C:47]1[CH:53]=[CH:52][C:50]([NH:51][C:1]([CH2:4][CH2:5][C:6]2[N:7]=[C:8]([F:30])[N:9]([C:11]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:10]=2)=[O:3])=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 20432338HCID 20432338, compound

Product 1

HCID 20432347HCID 20432347, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-carboxyethyl)-2-fluoro-1-triphenylmethylimidazole in CH2Cl2 was treated with triethylamine. The mixture was cooled, isobutyl chloroformate added, and stirred for 25 min. 4-Chloroaniline was then added, and stirring continued for 1 hour. Extractive work-up, followed by chromatography, gave 4-[2-(4-chlorophenylcarbamoyl)ethyl]-2-fluoro-1-triphenylmethylimidazole, having the following n.m.r. spectrum in CDCl3 +d6DMSO: 2.4-2.75 (m, 4H); 6.25 (s, 1H); 6.9-7.65 (m, 19H); 9.9 (br s, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. stirringstirring
  3. waitcontinued for 1 hour

Sources & evidence

ORD record
ord-b459df4cbb6c4dd8a079af2bef0465df
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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