Thiourea → 2-Carbamimidoylsulfanyl-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamide

HRID 1667654Notes

Reaction equation

HRID 1667654 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH:6]([C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])[C:7]([NH2:9])=[O:8]>C(O)C>[C:2]([S:3][CH:6]([C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:18])([F:19])[F:20])[C:7]([NH2:9])=[O:8])(=[NH:4])[NH2:1]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 866427942-Bromo-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamide

Product 1

HCID 866427932-Carbamimidoylsulfanyl-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamideYield 10.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.80 g (0.37 mole) of thiourea in 1200 mL of ethanol was added 11.40 g (0.37 mole) of 2-bromo-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamide. After stirring at room temperature overnight, the mixture was concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with dichloromethane-methanol (gradient 100:0-80:20) gave 11.80 g of 2-carbamimidoylsulfanyl-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamide as a yellow solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customPurification of the residue by silica gel chromatography
  3. washeluting with dichloromethane-methanol (gradient 100:0-80:20)

Sources & evidence

ORD record
ord-041e0679993d48a8b60dd66400b4fd59
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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