Water → 5-Chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 900863

反応式

HRID 900863 の反応式
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[Cl:7][C:8]1[S:12][C:11]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C.O>O1CCOCC1>[OH:4][CH2:3][C:2]([NH:1][S:13]([C:11]1[S:12][C:8]([Cl:7])=[C:9]([N+:17]([O-:19])=[O:18])[CH:10]=1)(=[O:15])=[O:14])([CH3:6])[CH3:5]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chloride

生成物 1

HCID 672187905-Chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide収率 30.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 2-amino-2-methyl-1-propanol (0.75 g, 8.39 mmol) in dioxane (21 ml) was added at room temperature 5-chloro-4-nitrothiophene-2-sulfonyl chloride (2.0 g, 7.63 mmol) and triethylamine (1.17 ml, 8.39 mmol). The light yellow suspension was stirred at room temperature for 17 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) and subsequent crystallization from ethyl acetate/hexane to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (0.73 g, 30%) as a light brown solid. MS (ISP) 313.1 [(M−H)−], mp 136° C.

後処理

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) and subsequent crystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-8b31cd04e9304f60aec365b95f3f653a
出典データセット
uspto-grants-2008_04
特許番号
US07361659B2

関連ノート

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