Water → HCID 56990876, 화합물

HRID 635261노트

반응식

HRID 635261 반응식
N1C=CC=CC=1.[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][CH2:9][CH2:8]1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[CH:21]=[CH:22][C:23](Cl)=[O:24].O>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:23]([N:10]2[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:7][CH2:8][CH2:9]2)=[O:24])[CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 53411290HCID 53411290, 화합물

생성물 1

HCID 56990876HCID 56990876, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Pyridine (25 ml) was added to a mixture of 3,4-dihydro-2H-1,4-benzoxazine (17.8 g) in DCM (200 ml). The mixture was cooled on an ice bath and poured out into a mixture of m-chloro-cinnamoyl chloride (33 g) in DCM (100 ml). The mixture was stirred at room temperature overnight. Water was added and the mixture was decanted. The organic layer was dried, filtered and the solvent was evaporated till dryness, to give a residue which was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 80/20) and recrystallisation from ACN/diethyl ether, yielding 26g (65.8%) of 4-[3-(3-chlorophenyl)-1-oxo-2-propen-1-yl]-2,3-dihydro-4H-1,4-benzoxazine (interm. 51).

후처리

  1. temperatureThe mixture was cooled on an ice bath
  2. customthe mixture was decanted
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customto give a residue which
  7. customwas purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 80/20) and recrystallisation from ACN/diethyl ether

출처 및 근거

ORD 기록
ord-4968c0ec1cc146b7974283ebf9bb95b7
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187786B1

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