Sodium Hydroxide → 3-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 659686

反応式

HRID 659686 の反応式
[Br:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[OH-].[Na+].Br[CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:21]=[C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:19][C:18]=2[S:26]([NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:28])=[O:27])[CH:14]=[CH:15][CH:16]=1>CS(C)=O.C(Cl)Cl>[Br:1][C:2]1[N:3]([CH2:10][C:11]2[CH:12]=[C:13]([C:17]3[CH:21]=[C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:19][C:18]=3[S:26]([NH:29][C:30]([CH3:32])([CH3:31])[CH3:33])(=[O:27])=[O:28])[CH:14]=[CH:15][CH:16]=2)[CH:4]=[CH:5][N:6]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 27732612-Bromo-1H-imidazoleHCID 670039813-(3-Bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

生成物 1

HCID 671329713-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide収率 99%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-bromoimidazole (68.9 mg, 0.469 mmol; see step (a)) in DMSO (1 mL) and NaOH (32.8 mg, 0.82 mmol), that had been stirred for 40 min at ambient temperature, was added a solution of 3-(3-bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (173.6 mg, 0.391 mmol; see Example 1(e)) in DMSO (1 mL) dropwise. The reaction mixture was stirred for 1 h at ambient temperature and then diluted with CH2Cl2 (15 mL). The organic layer was washed with water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (3:97) as eluent to give the sub-title compound in 99% yield as a colourless syrup (197.3 mg, 0.387 mmol).

後処理

  1. washThe organic layer was washed with water
  2. dry with materialdried (over anhydrous MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography

出典と根拠

ORDレコード
ord-65988bf132aa4dc887dfc212dc2bf758
出典データセット
uspto-grants-2011_12
特許番号
US08080571B2

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