(3-Trifluoromethylphenyl)urea → HCID 59218318, compound

HRID 1366251Notes

Reaction equation

HRID 1366251 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].[CH3:25][CH:26]([CH3:33])[C:27](=[O:32])[CH2:28][C:29](=O)[CH3:30]>O1CCCC1>[C:27]([C:28]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:29]=1[CH3:30])(=[O:32])[CH:26]([CH3:33])[CH3:25]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 1389845-Methyl-2,4-hexanedione (enol)

Product 1

HCID 59218318HCID 59218318, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-[3-(trifluoromethyl)phenyl]urea (6.37 g, 31.2 mmol), 4-cyanobenzaldehyde (4.09 g, 31.2 mmol) and 5-methylhexane-2,4-dione (4.0 g, 31.2 mmol) in tetrahydrofuran (150 ml) is added ethyl polyphosphonate (12 g). 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-098e974d905047118c3dc6f9e58cbe9b
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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