Triethylamine → N-{2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}acetamide

HRID 425403Notes

Reaction equation

HRID 425403 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:35][C:36](=[O:38])[CH3:37])[C:24]2[NH:25][CH:26]=[C:27]([CH2:29][C:30]([CH3:34])([CH3:33])[CH2:31][CH3:32])[N:28]=2)=[CH:18][CH:17]=1>C(Cl)Cl.O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:35][C:36](=[O:38])[CH3:37])[C:24]2[N:25]([S:10]([N:9]([CH3:14])[CH3:8])(=[O:12])=[O:11])[CH:26]=[C:27]([CH2:29][C:30]([CH3:34])([CH3:33])[CH2:31][CH3:32])[N:28]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 178442428HCID 178442428, compound

Product 1

HCID 66705710N-{2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.48 mL, 34.5 mmol) followed by dimethylsulfamoyl chloride (0.24 mL, 46 mmol) were added to an ambient temperature solution of N-{2-(4-bromophenyl)-1-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}acetamide (450 mg, 11.5 mmol) in methylene chloride (10 mL). After stirring at ambient temperature overnight, the reaction mixture was diluted with water and extracted with ethyl acetate and methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% acetone/methylene chloride afforded N-{2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}acetamide.

Workup

  1. extractionextracted with ethyl acetate and methylene chloride
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ae6205817d04265ac554a21d8f4093f
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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