Ammonia → N-(5-chloro-2-nitrophenyl)urea

HRID 657017Notes

Reaction equation

HRID 657017 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH:20]=1)[NH2:19].[NH3:24]>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([NH:19][C:5]([NH2:24])=[O:11])[CH:20]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 742185-Chloro-2-nitroanilineHCID 94429Triphosgene

Product 1

HCID 68810151N-(5-chloro-2-nitrophenyl)ureaYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of triphosgene (3.613 g, 12.175 mmol) in toluene (15 ml) was added a solution of 5-chloro-2-nitroaniline (2.100 g, 12.175 mmol) in toluene (15 ml) over 0.5 h and then the reaction was heated at 80° C. for 24 h. The reaction was then cooled and carefully poured onto aqueous NH3. This mixture was stirred for 1 h, filtered, washed with water (100 ml), MeOH (50 ml) and ethyl acetate (50 ml) to leave the desired product as a yellow solid (1.558 g, 60%).

Workup

  1. temperatureThe reaction was then cooled
  2. filtrationfiltered
  3. washwashed with water (100 ml), MeOH (50 ml) and ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-38fcfac85a1a47d69f06600f339a3d19
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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