Sulfuryl chloride → (2E)-2-[2-(4-chlorophenoxy)phenyl]-2-methoxyimino-N-methylacetamide

HRID 1491977

Reaction equation

HRID 1491977 reaction equation
[CH3:1][NH:2][C:3](=[O:21])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:5]/[O:6][CH3:7].S(Cl)([Cl:25])(=O)=O>ClCCl.O>[CH3:1][NH:2][C:3](=[O:21])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:25])=[CH:19][CH:20]=1)=[N:5]/[O:6][CH3:7]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 5483872(2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide

Product 1

HCID 19429863(2E)-2-[2-(4-chlorophenoxy)phenyl]-2-methoxyimino-N-methylacetamideYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-N-methyl-2-(2-phenoxyphenyl)-2-methoxyiminoacetamide (500 mg) in dichloromethane was cooled to 0° C., and sulfuryl chloride (285 mg) was dropwise added thereto. The resultant mixture was stirred at the same temperature for 2 hours, diluted with water and extracted with diethyl ether. The solvent was dried and removed, and the residue was subjected to HPLC with a mixture of hexane and ethyl acetate to give 382 mg of the objective compound.

Workup

  1. extractionextracted with diethyl ether
  2. customThe solvent was dried
  3. customremoved
  4. additionthe residue was subjected to HPLC with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-e1b54a6892ab41e7b12785ca4b4efe79
Source dataset
uspto-grants-1994_12
Patent number
US05371222

Linked notes

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