3-Chloropropanesulphonyl chloride → N-{5-[3-(1,1-dioxido-2-isothiazolidinyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

HRID 18432

反応式

HRID 18432 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:11]3)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:34][CH2:35][CH2:36][S:37](Cl)(=[O:39])=[O:38].[H-].[Na+]>CN(C)C=O>[O:38]=[S:37]1(=[O:39])[CH2:36][CH2:35][CH2:34][N:1]1[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:11]3)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 154103-Chloropropanesulphonyl chlorideHCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 46899970N-[5-(3-aminophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

生成物 1

HCID 11575686N-{5-[3-(1,1-dioxido-2-isothiazolidinyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide収率 9.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-[5-(3-aminophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.30 mmol), and diisopropylethylamine (79 mg, 0.61 mmol), in dry dimethylformamide (2 ml) was treated with 3-chloropropanesulfonyl chloride (54 mg, 0.30 mmol) and stirred at room temperature for 1 h. Sodium hydride (60% dispersion in oil, 15 mg, 0.38 mmol) was added and the mixture stirred at 60° C. for 0.5 h. The reaction mix was cooled then partitioned between dichloromethane and 0.5M hydrochloric acid, and the organic layer was evaporated under reduced pressure to give a brown oil which was purified by column chromatography on a 5 g isolute silica sep-pak column eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether to give the title compound as a yellow oil (12 mg, 9%).

後処理

  1. stirringthe mixture stirred at 60° C. for 0.5 h
  2. additionThe reaction mix
  3. temperaturewas cooled
  4. customthen partitioned between dichloromethane and 0.5M hydrochloric acid
  5. customthe organic layer was evaporated under reduced pressure
  6. customto give a brown oil which
  7. customwas purified by column chromatography on a 5 g isolute silica sep-pak column
  8. washeluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

出典と根拠

ORDレコード
ord-cf415d9399974ffea9b7863d9a6fca64
出典データセット
uspto-grants-2010_06
特許番号
US07741351B2

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