N-[2-(2-chloroethoxy)-phenylsulfonyl]-N'-methylurea → 2-(2-Chloroethoxy)benzene-1-sulfonyl isocyanate

HRID 1981253Notes

Reaction equation

HRID 1981253 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15](NC)=[O:16])(=[O:13])=[O:12]>ClC1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:12])=[O:13]

Participants

3

Reactant 1

HCID 20191437N-[2-(2-chloroethoxy)-phenylsulfonyl]-N'-methylurea

Product 1

HCID 194184142-(2-Chloroethoxy)benzene-1-sulfonyl isocyanateYield 98.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

12.5 g of N-[2-(2-chloroethoxy)-phenylsulfonyl]-N'-methylurea are suspended in 210 ml of chlorobenzene. This suspension is dried by azeotropic destilling off 20 ml of the solvent. 7.0 g of phosgene are introduced into the reaction mixture within 45 minutes at a temperature of 120°-130° C. Evaporation to dryness of the resulting clear solution yields 11.0 g of 2-(2-chloroethoxy)-phenylsulfonyl isocyanate in form of a yellowish oil.

Workup

  1. dry with materialThis suspension is dried by azeotropic destilling off 20 ml of the solvent
  2. addition7.0 g of phosgene are introduced into the reaction mixture within 45 minutes at a temperature of 120°-130° C
  3. customEvaporation to dryness of the resulting clear solution

Sources & evidence

ORD record
ord-a741d98c4758435086ef2f026f79328b
Source dataset
uspto-grants-1985_04
Patent number
US04514212

Reaction notes

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