Triethylamine → N-[2-(3,3,3-trifluoro-1propen-1-yl)phenylsulfonyl]-N'-methylurea

HRID 868455Notes

Reaction equation

HRID 868455 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12].[CH3:17][N:18]=[C:19]=[O:20].C(N(CC)CC)C>C(Cl)Cl>[F:16][C:2]([F:1])([F:15])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:19]([NH:18][CH3:17])=[O:20])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 53741182Benzenesulfonamide, 2-(3,3,3-trifluoro-1-propenyl)-

Product 1

HCID 53782727N-[2-(3,3,3-trifluoro-1propen-1-yl)phenylsulfonyl]-N'-methylureaYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g of 2-(3,3,3-trifluoro-1-propen-1-yl)phenylsulfonamide and 1.7 g of methyl isocyanate are suspended in 25 ml of methylene chloride and 3.0 g of triethylamine are added dropwise for 10 minutes, whereupon a clear solution forms. The solution is concentrated, the residue is dissolved in a 5% sodium carbonate solution, and insoluble constituents are removed by filtration. The clear solution is acidified with 10% hydrochloric acid, to give 5.9 g of N-[2-(3,3,3-trifluoro-1-propen-1-yl)phenylsulfonyl]-N'-methylurea is a colorless precipitate with a melting point of 190°-192° C.

Workup

  1. concentrationThe solution is concentrated
  2. dissolutionthe residue is dissolved in a 5% sodium carbonate solution, and insoluble constituents
  3. customare removed by filtration

Sources & evidence

ORD record
ord-cc3423b7d36648d3be0ff29f5176080a
Source dataset
uspto-grants-1988_10
Patent number
US04780125

Reaction notes

Loading…