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Butyl isocyanate → N-(Butylamino)carbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

HRID 1644853
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HRID 1644853 반응식
[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]([N:32]=[C:33]=[O:34])[CH2:29][CH2:30][CH3:31].C(NS(C1SC(CC(C)C)=CC=1C1C=CC(CN2C=CN=C2)=CC=1)(=O)=O)(C)(C)C>CC(C)=O.C(OCC)(=O)C>[CH2:28]([NH:32][C:33]([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])[CH2:29][CH2:30][CH3:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8110Butyl isocyanateHCID 14798Sodium HydroxideHCID 113947443(4-Imidazol-1-ylmethylphenyl)5-iso-butylthiophene-2 sulfonamideHCID 114190423-(4-Imidazol-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

생성물 1

HCID 10227337N-(Butylamino)carbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide수율 33%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

The crude product from step (c) above was dissolved in acetone (5 mL) under N2 (g). NaOH (0.20 mL, 1M, 0.20 mmol) was added to the mixture, which was then stirred for 10 min. Butyl isocyanate (109 μL, 0.97 mmol) was then added and the mixture was stirred overnight 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. Purification using column chromatography with CHCl3:MeOH (10:1) as eluent yielded the title compound (15.1 mg, 0.032 mmol) in 33% yield (from 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonic acid tert-butylamide).

후처리

  1. stirringthe mixture was stirred overnight 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. customPurification

출처 및 근거

ORD 기록
ord-f349ccd448764fecb3e7ee660c57d58a
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08124638B2

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