Dimethyl Sulfide → (3-(Methylthio)-1H-indol-6-yl)(morpholino)methanone

HRID 630440노트

반응식

HRID 630440 반응식
[CH3:1][S:2][CH3:3].ClN1C(=O)CCC1=O.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[CH:19]=2)C=[CH:13]1>ClCCl>[CH3:1][S:2][C:3]1[C:15]2[C:20](=[CH:19][C:18]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])=[CH:17][CH:16]=2)[NH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 39710543(1H-Indol-6-yl)(morpholino)methanone

생성물 1

HCID 118666043(3-(Methylthio)-1H-indol-6-yl)(morpholino)methanone수율 58.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-20 °C

실험 절차

Dimethylsulfane (8.17 mL, 109.32 mmol, 1.1 eq) was added dropwise to a stirred suspension of N-chlorosuccinimide (14.53 g, 109.32 mmol, 1.1 eq) in dichloromethane (50 mL) at 0° C. The reaction mixture was cooled to −20° C. and (1H-indol-6-yl)(morpholino)methanone (16.0 g, 99.37 mmol, 1.0 eq) in dichloromethane (120 mL) was added dropwise. After stirring for 1 h at room temperature, the solvent was evaporated and replaced by xylene (100 mL). The mixture was refluxed for 1 h, cooled to ambient temperature and then passed through a silica gel column [100-200 mesh, methanol/dichloromethane=1:19]. The product (16.0 g) obtained was used without further purification.

후처리

  1. customthe solvent was evaporated
  2. temperatureThe mixture was refluxed for 1 h
  3. temperaturecooled to ambient temperature

출처 및 근거

ORD 기록
ord-f1f9242d834b4f85b14e3d0338e98e46
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315490B2

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