Dimethyl Sulfoxide → trans-7-Chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde

HRID 1805

Reaction equation

HRID 1805 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:20](=[O:27])[C@@H:19]([CH2:28][CH2:29][OH:30])[O:18][C@H:17]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[C:16]=2[CH:38]=1>ClCCl.O.C(N(CC)CC)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:20](=[O:27])[C@@H:19]([CH2:28][CH:29]=[O:30])[O:18][C@H:17]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[C:16]=2[CH:38]=1

Participants

7

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 69945756trans-7-Chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol

Product 1

HCID 86752223trans-7-Chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehydeYield 64.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Procedure

To 25 ml of dichloromethane solution containing 0.70 ml of oxalyl chloride was added 5 ml of dichloromethane solution containing 0.71 ml of dimethylsulfoxide at -78° C., followed by stirring for 5 minutes. To the solution was slowly added 10 ml of dichloromethane solution containing 1.69 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol obtained in Example 160, followed by stirring for 15 minutes at -78° C. To the reaction mixture was added 2.79 ml of triethylamine and the mixture was further stirred for one hour at 0° C. and for 1.5 hours at room temperature. After the addition of 100 ml of water, extraction was performed with 100 ml of dichloromethane. The dichloromethane layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure. The residue was purified by column chromatography using silica gel (eluent, hexane:ethyl acetate=1:1) to give 1.08 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde as light-yellow crystals, m.p. 173° to 176° C.

Workup

  1. stirringby stirring for 15 minutes at -78° C
  2. stirringthe mixture was further stirred for one hour at 0° C. and for 1.5 hours at room temperature
  3. washThe dichloromethane layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-77f2d3d356f745ffa41558ea6f3bd9f3
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Linked notes

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