Dimethylformamide → HCID 86035948, 화합물

HRID 1678126노트

반응식

HRID 1678126 반응식
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[S:11]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C:17]2=O)=[CH:12]1>ClCCl.N1C=CC=CC=1>[Cl:3][C:17]1[N:16]([C:13]2[CH:14]=[CH:15][S:11][CH:12]=2)[C:24]2[C:19]([C:18]=1[CH:8]=[O:9])=[CH:20][CH:21]=[CH:22][CH:23]=2

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 148193781-(Thiophen-3-yl)-1,3-dihydro-2H-indol-2-one

생성물 1

HCID 86035948HCID 86035948, 화합물수율 57%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

반응 조건

온도
2.5 °C

실험 절차

Phosphorous oxychloride (1.9 mL, 20.9 mmol) is added slowly to a stirred solution of dimethylformamide (2 mL) and dichloromethane (2 mL) cooled to 0-5° C. After 5 min, a solution of the above 1-(thien-3-yl)-1H-indol-2-one (1.0 g, 2.65 mmol), pyridine (1 mL) and dichloromethane (4 mL) is added and the reaction is stirred at room temperature for 48 hr. The reaction mixture is poured into ice/water and extracted with ethyl acetate. Some solids are removed by filtration and the organic layer is separated, dried, filtered and concentrated. The residue is purified by chromatography eluting with pentane-10% ethyl acetate. Product containing fraction are combined and concentrated to afford 2-chloro-1-(thien-3-yl)-1H-indole-3-carboxaldehyde (694 mg, 57%) as a light orange solid. MS 262 (M+H).

후처리

  1. extractionextracted with ethyl acetate
  2. customSome solids are removed by filtration
  3. customthe organic layer is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography
  8. washeluting with pentane-10% ethyl acetate
  9. additionProduct containing fraction
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b866101aaf18450d83c5c75dfcad1907
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008491B2

반응 노트

불러오는 중…