Water → HCID 56990876, compound

HRID 635261Notes

Reaction equation

HRID 635261 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 56990876HCID 56990876, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4968c0ec1cc146b7974283ebf9bb95b7
Source dataset
uspto-grants-2001_02
Patent number
US06187786B1

Reaction notes

Loading…