(3-Trifluoromethylphenyl)urea → HCID 58674220, compound

HRID 2246389Notes

Reaction equation

HRID 2246389 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]([CH3:37])[CH2:27][C:28]([O:30][C@@H:31]([CH3:36])[C:32]([O:34][CH3:35])=[O:33])=[O:29]>C1COCC1>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[C:27]([C:28]([O:30][C@@H:31]([CH3:36])[C:32]([O:34][CH3:35])=[O:33])=[O:29])=[C:26]([CH3:37])[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:10](=[O:11])[NH:12]2)=[CH:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 54170392HCID 54170392, compound

Product 1

HCID 58674220HCID 58674220, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (0.98 mmol) N-[3-(trifluoromethyl)phenyl]urea, 129 mg (0.98 mmol) 4-cyanobenzaldehyde, 92 mg (0.49 mmol) (1S)-2-methoxy-1-methyl-2-oxoethyl 3-oxobutanoate, and 295 mg polyphosphoric acid ethyl ester are suspended in 3 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. A mixture of diastereoisomers is obtained.

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
  4. additionA mixture of diastereoisomers
  5. customis obtained

Sources & evidence

ORD record
ord-73850c71a4c94b69a99754f63bb9dbad
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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