Dimethyl Sulfoxide → HCID 19025026, compound

HRID 1033935Notes

Reaction equation

HRID 1033935 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]([C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=1)[C:13]([N:16]1[CH2:20][C:19]([CH3:21])=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]1=[O:28])([CH3:15])[CH3:14].C(N(CC)CC)C>ClCCl.O>[Cl:35][C:33]1[CH:34]=[C:29]([C:12](=[O:11])[C:13]([N:16]2[CH2:20][C:19]([CH3:21])=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]2=[O:28])([CH3:15])[CH3:14])[CH:30]=[C:31]([Cl:36])[CH:32]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19025024HCID 19025024, compound

Product 1

HCID 19025026HCID 19025026, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2.2 g (27.6 mmol) of dimethyl sulfoxide in 10 ml of dichloromethane was dropwise added over a period of 15 minutes at -60° C. to a solution of 2.65 g (20.8 mmol) of oxalyl dichloride in 40 ml of dichloromethane. A few minutes later, a solution of 5.4 g (13.8 mmol) of 1-[2-hydroxy-1,1-dimethyl-2-(3,5-dichlorophenyl)ethyl]-4-methyl-3-phenyl -3-pyrrolin-2-one in 20 ml of dichloromethane was dropwise added thereto at -60° C. The mixture was stirred at the same temperature for further 30 minutes. Then, 7 g (69 mmol) of triethylamine was dropwise added thereto, and the mixture was stirred at -60° C. for further 15 minutes. The reaction solution was restored to room temperature, and 20 ml of water was added thereto. The mixture was thoroughly stirred. The organic layer was treated by a conventional method, and crystals thereby obtained were washed with isopropyl ether to obtain 4.6 g (yield: 87%) of the desired product having a melting point of from 157° to 160° C.

Workup

  1. customat -60° C
  2. stirringthe mixture was stirred at -60° C. for further 15 minutes
  3. customwas restored to room temperature
  4. stirringThe mixture was thoroughly stirred
  5. additionThe organic layer was treated by a conventional method, and crystals
  6. customthereby obtained
  7. washwere washed with isopropyl ether

Sources & evidence

ORD record
ord-2b09f016245f46dc9cb102fc21337c74
Source dataset
uspto-grants-1994_05
Patent number
US05312929

Reaction notes

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