Sodium Hydroxide → N-butylsulfonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

HRID 1993863Notes

Reaction equation

HRID 1993863 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:17]=[C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[S:15][C:14]=3[S:22]([NH2:25])(=[O:24])=[O:23])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].[CH2:28]([S:32](Cl)(=[O:34])=[O:33])[CH2:29][CH2:30][CH3:31]>C1COCC1.C(OCC)(=O)C>[CH2:28]([S:32]([NH:25][S:22]([C:14]1[S:15][C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:17][C:13]=1[C:10]1[CH:11]=[CH:12][C:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:8][CH:9]=1)(=[O:24])=[O:23])(=[O:34])=[O:33])[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 754301-Butanesulfonyl chlorideHCID 113947443(4-Imidazol-1-ylmethylphenyl)5-iso-butylthiophene-2 sulfonamide

Product 1

HCID 10300357N-butylsulfonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide (prepared according to the procedure described in Example 10(c) above) was dissolved in THF (3 mL) under N2 (g). NaOH (1.0 mL, 1M, 1.0 mmol) was added to the mixture, which was then stirred for 10 min. Butanesulfonyl chloride (45 μL, 0.35 mmol) was then added, and the mixture was stirred for 24 h at room temperature. The reaction mixture was then diluted with ethyl acetate (150 mL) and washed with water and brine. The organic phase was dried over MgSO4 and the solvent was removed in vacuo. The crude product was recrystallised from acetone to yield the title compound (31.7 mg, 0.064 mmol).

Workup

  1. stirringthe mixture was stirred for 24 h at room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe crude product was recrystallised from acetone

Sources & evidence

ORD record
ord-dc3ae0ea65694c9585cddc993976bde3
Source dataset
uspto-grants-2010_01
Patent number
US07652054B2

Reaction notes

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