Chloroform → HCID 86745929, compound

HRID 893212Notes

Reaction equation

HRID 893212 reaction equation
[I-].[CH3:2][S+:3]([CH3:6])([CH3:5])=[O:4].[H-].[Na+].[H][H].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1.C(Cl)(Cl)Cl>CS(C)=O.ClC1C=CC=CC=1NC(=O)C=S(C)(C)=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:20])[CH:2]=[S:3]([CH3:6])([CH3:5])=[O:4])=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 6212ChloroformHCID 76934-Chlorophenyl IsocyanateHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 178418361HCID 178418361, compound

Product 1

HCID 86745929HCID 86745929, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 86745930HCID 86745930, compoundSolvent

Procedure

A solution of 22.0 grams (0.10 mole) of trimethylsulfoxonium iodide in 150 milliliters of dimethylsulfoxide was stirred, with cooling at 20° C., while 4.0 grams (0.10 mole) of 60% sodium hydride were added to the mixture in portions. Stirring was continued until hydrogen evolution was complete and a solution of 15.36 grams (0.10 mole) of 4-chlorophenyl isocyanate then added over a 30 minute period. After stirring for about 2.5 hours the reaction mixture was poured into 200 milliliters of ice water causing precipitation of a white solid. The latter was air dried and then extracted repeatedly with benzene followed by hot ethanol. The solid remaining undissolved following the third ethanol wash was washed with chloroform giving 6.72 grams (0.03 mole) of N-(chlorophenyl)-2-(dimethyloxosulfuranylidene)acetamide as the insoluble residue. Similar chloroform extractions of two crops of solid which separated from the final ethanol extract afforded an additional 1.58 grams (0.01 mole) of N-(4-chlorophenyl)-2-(dimethyloxosulfuranylidene)acetamide as the insoluble residue.

Workup

  1. additionwere added to the mixture in portions
  2. stirringAfter stirring for about 2.5 hours the reaction mixture
  3. customdried
  4. extractionextracted repeatedly with benzene
  5. washwash
  6. extractionSimilar chloroform extractions of two crops of solid which
  7. customseparated from the final ethanol
  8. extractionextract

Sources & evidence

ORD record
ord-1efd24d95d7f430c85784d21dd41aaa0
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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