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Water → 4-[[(4-Chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]amino]butanoic acid methyl ester

HRID 2054681
Notes
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Reaction equation

HRID 2054681 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:32]=[CH:31][C:15]3[N:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:18][C:14]=3[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:35][O:36][C:37](=[O:42])[CH2:38][CH2:39][CH2:40]Br.O>CN(C)C=O>[CH3:35][O:36][C:37](=[O:42])[CH2:38][CH2:39][CH2:40][N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[C:12]1[CH:32]=[CH:31][C:15]2[N:16]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:18][C:14]=2[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 107604Methyl 4-bromobutyrateHCID 219380284-Chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide

Product 1

HCID 673640314-[[(4-Chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]amino]butanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

100 mg of 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, mixed with 6 mg of sodium hydride and stirred for 30 minutes at 20° C. 56 mg of 4-bromobutyric acid methyl ester was added, it was allowed to stir for 15 hours, mixed with water, extracted three times with ethyl acetate, the extracts were dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was digested with diisopropyl ether.

Workup

  1. stirringto stir for 15 hours
  2. extractionextracted three times with ethyl acetate
  3. customthe extracts were dried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-6331a12aacbe4bc8a50f32aed5c1cc70
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07329679B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes