Thiourea → 5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl-carbamimidothioic acid methyl ester hydrobromide

HRID 854125Notes

Reaction equation

HRID 854125 reaction equation
[Br:1][CH2:2][C:3]1[C:4]([C:13]([F:16])([F:15])[F:14])=[N:5][N:6]([CH3:12])[C:7]=1[O:8][CH:9]([F:11])[F:10].[NH2:17][C:18]([NH2:20])=[S:19]>C(O)C>[BrH:1].[F:10][CH:9]([F:11])[O:8][C:7]1[N:6]([CH3:12])[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[C:3]=1[CH2:2][S:19][C:18](=[NH:17])[NH2:20]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 117228384-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 230756895-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl-carbamimidothioic acid methyl ester hydrobromideYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 19.1 g (purity: 75.0%, 46.3 mmol) of 4-bromomethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole in 30 ml of ethanol was added 3.5 g (46.3 mmol) of thiourea, followed by 1 hour of heating and refluxing under stirring. The solvent was removed by evaporation under reduced pressure and the residue was washed with a mixed solvent of ethyl acetate and n-hexane to obtain 13.8 g (yield: 77.5%) of 2-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethyl)-isothiourea hydrobromide as white crystals (melting point: 130 to 131° C.).

Workup

  1. temperatureof heating
  2. temperaturerefluxing
  3. customThe solvent was removed by evaporation under reduced pressure
  4. washthe residue was washed with a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-74384e3f3db14e058e054bddbf1220ed
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

Loading…