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

HRID 325807Notes

Reaction equation

HRID 325807 reaction equation
[Cl:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH2:15])(=[O:14])=[O:13])=[CH:3][Cl:4].[CH3:16][N:17]=[C:18]=[O:19].C(N(CC)CC)C>C(Cl)Cl>[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:18]([NH:17][CH3:16])=[O:19])(=[O:13])=[O:14])=[CH:3][Cl:4]

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'-methylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 6.7 g of 2-(1,2-dichlorovinyloxy)phenylsulfonamide in 50 ml of methylene chloride is treated with 1.9 g of methyl isocyanate. 3.3 g of triethylamine are added dropwise to this mixture at a temperature of 20°-25° C. within 10 minutes resulting in a clear solution. The solution is stirred for a further hour and evaporated to dryness. The residue is solved in 5% aqueous sodium coarbonate and acidified with a 10% solution of hydrochloric acid yielding 7.8 g of N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-methyl urea, m.p. 225°-226° C.

Workup

  1. customresulting in a clear solution
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-58f3ee4be5364d1e9cbe09ecf2911a93
Source dataset
uspto-grants-1984_04
Patent number
US04443245

Reaction notes

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