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Methyl iodide → 3-(Cyanomethyl)-N,N-dimethyl-1H-indole-5-ethanesulphonamide

HRID 982008
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HRID 982008 반응식
IC.CN([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH:14]=2)[NH:9][CH:8]=1)C.[C-:24]#[N:25].[K+]>CS(C)=O>[C:24]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][S:18]([N:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])[CH:14]=2)[NH:9][CH:8]=1)#[N:25]
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 9032Potassium CyanideHCID 134757383-[(Dimethylamino)methyl]-N,N-dimethyl-1H-indole-5-ethanesulphonamide

생성물 1

HCID 134757623-(Cyanomethyl)-N,N-dimethyl-1H-indole-5-ethanesulphonamide수율 51.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Iodomethane (1.1 ml) was added to a stirred solution of the product of Stage (iii) (2.7 g) in dry dimethylsulphoxide (30 ml) and the resulting solution stirred at room temperature for 10 min. Potassium cyanide (2.7 g) was added, and the resulting mixture stirred at room temperature overnight. The mixture was partitioned between sodium carbonate, (2N, 300 ml) and ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo to give an oil which was purified by `flash` chromatography (J, 5 cm col.) to give the title compound as a solid (1.3 g) m.p. 105°-107°.

후처리

  1. stirringthe resulting mixture stirred at room temperature overnight
  2. customThe mixture was partitioned between sodium carbonate, (2N, 300 ml) and ethyl acetate (2×100 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give an oil which
  6. customwas purified by `flash` chromatography (J, 5 cm col.)

출처 및 근거

ORD 기록
ord-598ebf8a9aef4c69b36c622c62aff7eb
출처 데이터셋
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04994483

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