Dimethyl Sulfoxide → 1-[2,4-Bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carbaldehyde

HRID 1620635노트

반응식

HRID 1620635 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]([F:35])([F:34])[C:13]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18][C:17]1=[O:25].[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[F:35][C:12]([F:11])([F:34])[C:13]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[C:17](=[O:25])[CH2:18][CH2:19][CH:20]([CH:23]=[O:24])[CH2:21][CH2:22]1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 866788011-[2,4-Bis(trifluoromethyl)benzyl]-5-(hydroxymethyl)azepan-2-one

생성물 1

HCID 866788021-[2,4-Bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carbaldehyde수율 46.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8471Triethylamine용매

실험 절차

To a solution of DMSO (1.40 g) in dichloromethane (100 mL) was slowly added a solution of oxalyl chloride (2.48 g) in dichloromethane (200 mL) at −78° C. The reaction mixture was stirred for 5 min, a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-5-(hydroxymethyl)azepan-2-one (6.0 g) in dichloromethane (100 mL) was added dropwise, and the mixture was stirred for 15 min. Triethylamine (8.2 g) was added and the mixture was allowed to warm to room temperature. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.76 g).

후처리

  1. stirringthe mixture was stirred for 15 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-fe932f345f2d47a3bc7fd82c2e807935
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772277B2

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