Urea → N-(Carbamoylcarbamothioyl)-4-chlorobenzamide

HRID 1752168Notes

Reaction equation

HRID 1752168 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]=[C:9]=[S:10])=[O:7])=[CH:4][CH:3]=1.[NH2:13][C:14]([NH2:16])=[O:15]>CC(C)=O>[C:14]([NH:16][C:9]([NH:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1)=[S:10])(=[O:15])[NH2:13]

Participants

4

Reactant 2

HCID 1176UreaHCID 2321624-Chlorobenzoyl isothiocyanate

Product 1

HCID 12582387N-(Carbamoylcarbamothioyl)-4-chlorobenzamideYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chlorobenzoyl isothiocyanate (395 mg) and 600 mg urea (5 equiv) were mixed in 30 mL of acetone and stirred at reflux for 1 day. The reaction was concentrated and the residue slurried in diethyl ether. The residue was collected by filtration and washed with diethyl ether. The white solid was dissolved in ethyl acetate (10 ml) and the resultant solution washed with water (10 ml) and brine (10 ml), dried over MgSO4, filtered and concentrated to a white solid (0.35 g, 1.4 mmol, 70% yield.

Workup

  1. temperatureat reflux for 1 day
  2. concentrationThe reaction was concentrated
  3. filtrationThe residue was collected by filtration
  4. washwashed with diethyl ether
  5. dissolutionThe white solid was dissolved in ethyl acetate (10 ml)
  6. washthe resultant solution washed with water (10 ml) and brine (10 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to a white solid (0.35 g, 1.4 mmol, 70% yield

Sources & evidence

ORD record
ord-fe371120aa564ab7b91f45e7ba280c97
Source dataset
uspto-grants-2015_10
Patent number
US09162994B2

Reaction notes

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