N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-methylurea → 2-[(1,2-Dichloroethenyl)oxy]benzene-1-sulfonyl isocyanate

HRID 325808Notes

Reaction equation

HRID 325808 reaction equation
[Cl:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16](NC)=[O:17])(=[O:14])=[O:13])=[CH:3][Cl:4]>ClC1C=CC=CC=1>[Cl:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([N:15]=[C:16]=[O:17])(=[O:13])=[O:14])=[CH:3][Cl:4]

Participants

3

Reactant 1

HCID 54175902N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-methylurea

Product 1

HCID 539300762-[(1,2-Dichloroethenyl)oxy]benzene-1-sulfonyl isocyanateYield 98.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

9.8 g of N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-methyl urea are solved in 200 ml of chlorobenzene. The solution is dried by azeotropic destilling off of 20 ml of the solvent. 5.3 g of phosgene are introduced into this solution within 45 minutes at a temperature of 120°-130° C. Evaporation of the reaction mixture to dryness yields 8.7 g of 2-(1,2-dichlorovinyloxy)phenylsulfonyl-isocyanate in form of a yellowish oil.

Workup

  1. customThe solution is dried
  2. addition5.3 g of phosgene are introduced into this solution within 45 minutes at a temperature of 120°-130° C
  3. customEvaporation of the reaction mixture to dryness

Sources & evidence

ORD record
ord-ee41dbffc72f4da1bd1d972451d298d7
Source dataset
uspto-grants-1984_04
Patent number
US04443245

Reaction notes

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