Thiourea → 2-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethyl)-isothiourea hydrochloride

HRID 854129Notes

Reaction equation

HRID 854129 reaction equation
[Cl: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>[ClH: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 230756834-(Chloromethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 230757032-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethyl)-isothiourea hydrochlorideYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.7 g (purity: 83.4%, 11.7 mmol) of 4-chloromethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole in 20 ml of ethanol was added 0.8 g (11.1 mmol) of thiourea, followed by stirring at room temperature overnight and further heating and stirring at 50° C. for 1 hour. The solvent was removed by evaporation under reduced pressure and the residue was washed with n-hexane to obtain 3.8 g (yield: 96.4%) of 2-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethyl)-isothiourea hydrochloride as white crystals (melting point: 117 to 119° C.)

Workup

  1. temperaturefurther heating
  2. stirringstirring at 50° C. for 1 hour
  3. customThe solvent was removed by evaporation under reduced pressure
  4. washthe residue was washed with n-hexane

Sources & evidence

ORD record
ord-ff324b24b64c43bb8ae39a914cef59fe
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

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