Chlorophenyl isocyanate → 1-(2-Chloro-phenyl)-3-(6-chloro-pyrimidin-4-yl)-urea

HRID 1038701Notes

Reaction equation

HRID 1038701 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[C:17]=[O:18]>C1COCC1>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]([NH:8][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[CH:6][N:5]=1)=[O:18]

Participants

4

Reactant 2

HCID 76833Chlorophenyl isocyanate2×HCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 860869821-(2-Chloro-phenyl)-3-(6-chloro-pyrimidin-4-yl)-ureaYield 174.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-chloro-pyrimidin-4-ylamine (997 mg, 7.7 mmol) and 2-chlorophenyl isocyanate (0.46 mL, 3.85 mmol) in THF (20 mL) is refluxed for 4 h. A further amount of 2-chlorophenyl isocyanate (0.46 mL, 3.85 mmol) is added and the reaction mixture is refluxed for 28 h. The reaction mixture is cooled to RT, the precipitate is filtered to afford the title compound (1.9 g, 86%).

Workup

  1. temperaturethe reaction mixture is refluxed for 28 h
  2. filtrationthe precipitate is filtered

Sources & evidence

ORD record
ord-783f840a770941c9856e0b181da665f4
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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