2-Chloroaniline → 7-Chloro-2-methyl-3-methylsulfanyl-1H-indole

HRID 23385

반응식

HRID 23385 반응식
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].ClOC(C)(C)C.[CH3:15][S:16][CH2:17][C:18](=O)[CH3:19].C(N(CC)CC)C>ClCCl.O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[NH:4][C:18]([CH3:19])=[C:17]2[S:16][CH3:15]

참가 물질

7

반응물 4

HCID 72402-ChloroanilineHCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 64307131-Methylthio-2-propanone

생성물 1

HCID 225739767-Chloro-2-methyl-3-methylsulfanyl-1H-indole

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매4회

반응 조건

온도
-65 °C

실험 절차

Using the procedure described in J. Amer. Chem. Soc., 1974, 96 (17) 5495 , 2-chloroaniline (1.27 g, 10 mmole) was dissolved in dichloromethane (35 ml) and cooled to −65° C. To this solution was added dropwise with vigorous stirring, t-butyl hypochlorite (1.08 g, 10 mmole) in dichloromethane (5 ml). After 10 minutes 1-methylsulfanyl-propan-2-one (1.04 g, 10 mmole) dissolved in dichloromethane (5 ml) was added. The mixture was stirred at −65° C. for 1 h more. At this point triethylamine (1.01 g, 10 mmole) dissolved in dichloromethane (5 ml) was added. Upon completion of the addition, the reaction mixture was allowed to reach ambient temperature. Water was added and the layers were separated, the organic layer was dried over magnesium sulfate, filtered and the solvent evaporated to dryness. The residue was purified by column chromatography on silica gel using a mixture of hexane-ethyl acetate (95:5) to elute 7-chloro-2-methyl-3-methylsulfanyl-1H-indole (1.94 g) as an oil.

후처리

  1. additionwas added
  2. additionwas added
  3. additionUpon completion of the addition
  4. customto reach ambient temperature
  5. customthe layers were separated
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated to dryness
  9. customThe residue was purified by column chromatography on silica gel using
  10. additiona mixture of hexane-ethyl acetate (95:5)
  11. washto elute 7-chloro-2-methyl-3-methylsulfanyl-1H-indole (1.94 g) as an oil

출처 및 근거

ORD 기록
ord-b4f5cb2c432f42aeafa008ca074bfba8
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852726B2

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