(3-Trifluoromethylphenyl)urea → HCID 59684832, compound

HRID 421808Notes

Reaction equation

HRID 421808 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].[Br:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:37])[CH2:33][C:34](=O)[CH3:35])=[CH:28][CH:27]=1>O1CCCC1>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([C:33]2[CH:21]([C:20]3[CH:23]=[CH:24][C:17]([C:15]#[N:16])=[CH:18][CH:19]=3)[NH:12][C:10](=[O:11])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=3)[C:34]=2[CH3:35])=[O:37])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 4326531-(4-bromophenyl)butane-1,3-dione

Product 1

HCID 59684832HCID 59684832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.23 g (20.74 mmol) N-[3-(trifluoromethyl)phenyl]urea, 2.72 g (20.74 mmol) 4-cyanobenzaldehyde, 5.00 g (20.74 mmol) 1-(4-bromophenyl)butane-1,3-dione and 6.5 g polyphosphoric acid ethyl ester are suspended in 50 ml of tetrahydrofuran. The mixture is stirred at reflux for 20 hours. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethyl acetate mixtures as eluent.

Workup

  1. temperatureat reflux for 20 hours
  2. customthe solvent is removed in vacuo
  3. customthe residue is purified by column chromatography on silica with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-b6ef96fb8dfa4df8b48d39d5d0ee7d67
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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