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

HRID 1038705Notes

Reaction equation

HRID 1038705 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH2:15])[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]=[C:24]=[O:25]>COCCOCCOC>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:25])[NH:15][C:13]1[CH:14]=[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:10]=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 66669982N~4~-(3-chlorophenyl)pyrimidine-4,6-diamine

Product 1

HCID 577103613-(2-Chloro-phenyl)-1-[6-(3-chloro-phenylamino)-pyrimidin-4-yl]-ureaYield 52.4%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of N-(3-chloro-phenyl)-pyrimidine-4,6-diamine (110 mg, 0.5 mmol) and 2-chlorophenyl isocyanate (60 μL, 0.5 mmol) in diglyme (1.5 mL) is stirred at 80° C. for 18 h. The precipitate which formed over time is filtered and washed with hexane/ethyl acetate to afford the pure title compound (98 mg, 52%).

Workup

  1. customThe precipitate which formed over time
  2. filtrationis filtered
  3. washwashed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-ca97c478f7ff4bce9922ea3cda22b7a0
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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