Urea → N-(Carbamoylcarbamothioyl)-4-chlorobenzamide

HRID 1995900Notes

Reaction equation

HRID 1995900 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]>C1COCC1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([NH:8][C:9]([NH:13][C:14](=[O:15])[NH2:16])=[S:10])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 2321624-Chlorobenzoyl isothiocyanate

Product 1

HCID 12582387N-(Carbamoylcarbamothioyl)-4-chlorobenzamideYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-Chlorobenzoylisothiocyanate (152.4 g) in THF (500 ml) is added dropwise to a stirred suspension of urea (46.3 g) in THF (750 ml). The reaction mixture is stirred over the weekend. The precipitate is filtered, washed with ether and dried leaving 101.7 g of a white solid, m.p. 155°-158° C. The filtrate is evaporated, filtered, the solid washed with ether and recrystallized from dioxane to give 7.8 g of additional white solid.

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-3e7bd0db155347d1823c5cafa6c36c7e
Source dataset
uspto-grants-1983_09
Patent number
US04406897

Reaction notes

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