Triethylamine → N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-methylurea

HRID 638640Notes

Reaction equation

HRID 638640 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH2:19])(=[O:18])=[O:17])=[CH:7][Cl:8].C(N(CC)CC)C>C(Cl)Cl>[Cl:5][C:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH:19][C:3]([NH:2][CH3:1])=[O:4])(=[O:17])=[O:18])=[CH:7][Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 537128512-[(1,2-Dichloroethenyl)oxy]benzene-1-sulfonamide

Product 1

HCID 54175902N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-methylureaYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.9 g of methyl isocyanate are added to a suspension of 6.7 g of 2-(1,2-dichlorovinyloxy)phenylsulfonamide in 50 ml of methylene chloride. 3.3 g of triethylamine are added dropwise to this mixture at 20° to 25° C. in the course of 10 minutes, a clear solution being formed. Stirring of this solution is continued for a further hour, and the solution is then evaporated to dryness. The residue is dissolved in 5% aqueous sodium carbonate solution and acidified with 10% hydrochloric acid, whereupon the product precipitates as crystals. After filtration and drying, 7.8 g of N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-methylurea are obtained. Melting point: 228°-229° C.

Workup

  1. customa clear solution being formed
  2. waitis continued for a further hour
  3. customthe solution is then evaporated to dryness
  4. dissolutionThe residue is dissolved in 5% aqueous sodium carbonate solution
  5. customprecipitates as crystals
  6. filtrationAfter filtration
  7. customdrying

Sources & evidence

ORD record
ord-ff766e98301c4422a8c30559b1946278
Source dataset
uspto-grants-1985_12
Patent number
US04562210

Reaction notes

Loading…