Triethylamine → ethyl 1H-indol-5-ylcarbamate

HRID 1467995노트

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HRID 1467995 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C.[CH2:18]([O:20][C:21](Cl)=[O:22])[CH3:19]>ClCCl>[CH2:18]([O:20][C:21](=[O:22])[NH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)[CH3:19]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 788675-Aminoindole

생성물 1

HCID 54033885ethyl 1H-indol-5-ylcarbamate수율 35.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 1H-indol-5-amine (11 g, 83.2 mmol) and triethyl amine (25.22 g, 250 mmol) in dichloromethane (110 mL) at −10° C., ethyl-chloro-formate (13.5 g 124.8 mmol) was added dropwise and stirred at 0° C. for 2-3 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the resultant residue was purified by flash column chromatography to give ethyl-1H-indol-5-ylcarbamate (5.980 g, 35.2%); MS: 205 (M+1).

후처리

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resultant residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-7af1d86742654a98bab712e45762843f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000175B2

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