Thiourea → p-Toluenesulfonate

HRID 618190Notes

Reaction equation

HRID 618190 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O:15][CH2:16][CH2:17][CH:18]=[C:19]([F:21])[F:20])(=[O:14])=[O:13])=[CH:8][CH:7]=1>C(O)C>[F:20][C:19]([F:21])=[CH:18][CH2:17][CH2:16][NH:1][C:2]([NH2:4])=[S:3].[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 11666101HCID 11666101, compound

Product 2

HCID 85570p-ToluenesulfonateYield 174.8%HCID 214789004,4-Difluorobut-3-enylthiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (0.29 g) and 4,4-difluorobut-3-enyl 4-methyl-benzenesulfonate (1 g) were heated together under reflux in ethanol (20 cm3) for 24 hours. The reaction mixture was cooled and the solvent evaporated under reduced pressure to give an oil which slowly crystallised. Trituration with hexane gave (4,4-difluorobut-3-enyl)-thiourea as its 4-methyl-benzenesulfonate salt (1.14 g). MH+ (FAB)=167; 1H NMR (DMSO-d6): δ 2.48(3H,s); 2.46-2.58(2H,m); 3.42(2H,t); 4.66-4.84(1H,m); 7.32(2H,d); 7.68(2H,d); 9.10-9.40(3H,br).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent evaporated under reduced pressure
  3. customto give an oil which
  4. customslowly crystallised

Sources & evidence

ORD record
ord-52a89cd40f7e4133bc288de8841ceed8
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Reaction notes

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