(3-Trifluoromethylphenyl)urea → HCID 59684870, compound

HRID 421809Notes

Reaction equation

HRID 421809 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].[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:39])[CH2:35][C:36](=O)[CH3:37])=[CH:30][CH:29]=1)([O-:27])=[O:26]>O1CCCC1>[N+:25]([C:28]1[CH:29]=[CH:30][C:31]([C:34]([C:35]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:36]=2[CH3:37])=[O:39])=[CH:32][CH:33]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 951621,3-Butanedione, 1-(4-nitrophenyl)-

Product 1

HCID 59684870HCID 59684870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.85 g (48.27 mmol) N-[3-(trifluoromethyl)phenyl]urea, 6.33 g (48.27 mmol) 4-cyanobenzaldehyde, 10.00 g (48.27 mmol) 1-(4-nitrophenyl)butane-1,3-dione and 15 g polyphosphoric acid ethyl ester are suspended in 100 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-43cc576d8deb4b6c94a33692ac7e456e
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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