Water → HCID 56990876、化合物

HRID 635261ノート

反応式

HRID 635261 の反応式
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

参加物

6

反応物 4

HCID 962WaterHCID 1049PyridineHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 53411290HCID 53411290、化合物

生成物 1

HCID 56990876HCID 56990876、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4968c0ec1cc146b7974283ebf9bb95b7
出典データセット
uspto-grants-2001_02
特許番号
US06187786B1

反応ノート

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