(3-Trifluoromethylphenyl)urea → HCID 68431415, compound

HRID 2246401Notes

Reaction equation

HRID 2246401 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].O=[C:26]([CH3:35])[CH2:27][C:28]([O:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29]>C1COCC1>[C:33]([CH2:32][CH2:31][O:30][C:28]([C:27]1[CH:21]([C:20]2[CH:23]=[CH:24][C:17]([C:15]#[N:16])=[CH:18][CH:19]=2)[NH:12][C:10](=[O:11])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)[C:26]=1[CH3:35])=[O:29])#[N:34]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 123604062-Cyanoethyl 3-oxobutanoate

Product 1

HCID 68431415HCID 68431415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.87 g (48.3 mmol) N-[3-(trifluoromethyl)phenyl]urea, 12.68 g (96.68 mmol) 4-cyanobenzaldehyde, 15 g (96.68 mmol) (2-cyanoethyl) 3-oxobutanoate and 37.5 g polyphosphoric acid ethyl ester are suspended in 250 ml of THF. The mixture is stirred at reflux for 18 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 as eluent.

Workup

  1. temperatureat reflux for 18 hours
  2. customthe solvent is removed in vacuo
  3. customthe residue is purified by column chromatography on silica with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-c5782e97bda0464283081990e05f4205
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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