Sodium hydride → methyl 3-chloro(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylate

HRID 901954ノート

反応式

HRID 901954 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:16][C:17]1[C:18]([Cl:26])=[C:19]([C:22]([O:24][CH3:25])=[O:23])[S:20][CH:21]=1.S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[Cl:26][C:18]1[C:17]([CH2:16][N:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[CH3:14])=[CH:21][S:20][C:19]=1[C:22]([O:24][CH3:25])=[O:23]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 2329924-Chloro-N-methylbenzenesulfonamideHCID 516920Potassium bisulfateHCID 18376575Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate

生成物 1

HCID 69208322methyl 3-chloro(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylate収率 102.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% dispersion, 150 mg, 3.8 mmol) was added to a solution of 4-chloro-N-methylbenzenesulfonamide (640 mg, 3.1 mmol) in DMF (12 ml) while cooling in an ice/water bath. After stirring for 15 min the mixture was allowed to warm to room temperature and stirred for a further 30 min. Methyl 4-bromomethyl-3-chlorothiophene-2-carboxylate (1.08 g, 4.0 mmol) was added and the mixture was stirred for 18 h. 0.3N Potassium hydrogen sulphate solution was added and the mixture evaporated. The mixture was extracted with ethyl acetate and the organic extract was washed with brine, dried and reduced. Chromatography (25% EtOAc/75% 60-80 pet ether) yielded methyl 3-chloro(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylate (1.25 g, 79%) as a white solid.

後処理

  1. temperaturewhile cooling in an ice/water bath
  2. stirringstirred for a further 30 min
  3. stirringthe mixture was stirred for 18 h
  4. customthe mixture evaporated
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionthe organic extract
  7. washwas washed with brine
  8. customdried

出典と根拠

ORDレコード
ord-337ed5aeaf244c55825edb2de5c57ca4
出典データセット
uspto-grants-2008_04
特許番号
US07365065B2

反応ノート

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