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

HRID 1419043Notes

Reaction equation

HRID 1419043 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]([CH:22]([CH3:24])[CH3:23])[C:20](=[O:25])[C@@H:19]([CH2:26][CH2:27][OH:28])[O:18][C@H:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:16]=2[CH:36]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH:22]([CH3:23])[CH3:24])[C:20](=[O:25])[C@@H:19]([CH2:26][CH:27]=[O:28])[O:18][C@H:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:16]=2[CH:36]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69945311trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol

Product 1

HCID 86752221trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehydeYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalyl chloride (0.72 ml) in methylene chloride (10 ml) was cooled to -65° C., to which was added dropwise a solution of dimethyl sulfoxide (0.63 ml) in methylene chloride (2 ml) taking 5 minutes, followed by stirring for 5 minutes. To the mixture was added dropwise, taking 15 minutes, a solution of trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol (2.5 g) obtained in Example 47 in methylene chloride (15 ml), which was stirred for 10 minutes. To the resultant mixture was added triethylamine (3.45 ml) taking 5 minutes, then the cooling bath was removed. The mixture was stirred for 10 minutes at room temperature, to which was then added 1N hydrochloric acid (50 ml), followed by stirring. The methylene chloride layer was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure to leave trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde (2.3 g) as an oily product.

Workup

  1. additionTo the mixture was added dropwise
  2. waittaking 15 minutes
  3. waittaking 5 minutes
  4. customthe cooling bath was removed
  5. stirringThe mixture was stirred for 10 minutes at room temperature, to which
  6. additionwas then added 1N hydrochloric acid (50 ml)
  7. stirringby stirring
  8. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e7bd5331d8344af29ef1e7cbd4951447
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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