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

HRID 901954노트

반응식

HRID 901954 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-337ed5aeaf244c55825edb2de5c57ca4
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365065B2

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