Trifluoroacetic acid → 3-(4-Imidazol-1-ylmethylphenyl)-5-butylthiophene-2-sulfonamide

HRID 1644833Notes

Reaction equation

HRID 1644833 reaction equation
FC(F)(F)C(O)=O.[N:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH3:28])[S:22][C:21]=3[S:29]([NH:32]C(C)(C)C)(=[O:31])=[O:30])=[CH:16][CH:15]=2)[CH:12]=[CH:11][N:10]=[CH:9]1.BrC1C=CC(CN2C=CN=C2)=CC=1>C1(OC)C=CC=CC=1>[N:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH3:28])[S:22][C:21]=3[S:29]([NH2:32])(=[O:31])=[O:30])=[CH:16][CH:15]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 29895571-(4-Bromobenzyl)-1H-imidazoleHCID 119940313-(4-Imidazol-1-ylmethylphenyl)-5-butyl-N-tert-butylthiophene-2-sulfonamide

Product 1

HCID 667751023-(4-Imidazol-1-ylmethylphenyl)-5-butylthiophene-2-sulfonamideYield 49%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

Trifluoroacetic acid was added (10 mL) to the crude 3-(4imidazol-1-ylmethylphenyl)-5-butyl-N-tert-butylthiophene-2-sulfonamide from step (c) above, and one drop (ca. 0.05 mL) of anisol was added to the mixture. The reaction mixture was stirred under N2 atmosphere for 30 hours and then evaporated and co-evaporated with acetonitrile. The crude product was purified by column chromatography (CH2Cl2:MeOH (20:1)) to give sub-title compound (232 mg, 0.62 mmol) in 49% yield (from 1-(4-bromobenzyl)-1H-imidazole).

Workup

  1. additionwas added to the mixture
  2. customevaporated
  3. customThe crude product was purified by column chromatography (CH2Cl2:MeOH (20:1))

Sources & evidence

ORD record
ord-bc4b42bdb04d418d9011c63cdec74c33
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

Loading…