Thiourea → HCID 86751487, compound

HRID 2292571Notes

Reaction equation

HRID 2292571 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>[S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH3:5])=[CH:7][CH:8]=1)([OH:15])(=[O:14])=[O:13].[F:20][C:19]([F:21])=[CH:18][CH2:17][CH2:16][NH:1][C:2]([NH2:4])=[S:3]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 11666101HCID 11666101, compound

Product 1

HCID 86751487HCID 86751487, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (0.29 g) and 4,4-difluoro-3-butenyl 4-methyl-benzenesulfonate (see Example 3B) (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-difluoro-3-butenyl)-thiourea tosylate salt (1.14 g). MH+ (FAB)=167; 1H NMR (DMSO): 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, broad)

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-d9476952efb448fab95deb891a844374
Source dataset
uspto-grants-1997_11
Patent number
US05684011

Reaction notes

Loading…