Chloroform → N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-{[3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl]methyl}urea

HRID 705109Notes

Reaction equation

HRID 705109 reaction equation
[NH2:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:11](=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1.C(Cl)(Cl)[Cl:35]>>[Cl:35][C:28]1[CH:27]=[CH:26][C:25]([NH:29][C:30]([NH:1][CH2:2][C:3]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:11](=[O:20])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[O:31])=[CH:24][C:23]=1[C:22]([F:32])([F:33])[F:21]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 3872314HCID 3872314, compound

Product 1

HCID 9913498N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-{[3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl]methyl}ureaYield 98%

Procedure

To a mixture of the amine (4) (14 mg, 0.05 mmol) in chloroform (0.5 mL), was added 3-trifluoromethylphenyl isocyanate (10 mg, 0.05 mmol). After stirring overnight the solvent was removed in vacuo, triturated with hexanes, filtered and dried to give the title urea (5) (24 mg, 98%) as a white solid:

Workup

  1. customwas removed in vacuo
  2. customtriturated with hexanes
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-7d92d471d6b24c96a4cd1b9896313871
Source dataset
uspto-grants-2015_11
Patent number
US09173869B2

Reaction notes

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