4-Nitrobenzaldehyde → HCID 58674197, compound

HRID 2246402Notes

Reaction equation

HRID 2246402 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.[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16].O=[C:27]([CH3:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1>[CH3:34][C:27]1[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:10](=[O:11])[NH:12][CH:22]([C:21]2[CH:24]=[CH:25][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 8868Ethyl AcetoacetateHCID 25712(3-Trifluoromethylphenyl)urea

Product 1

HCID 58674197HCID 58674197, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.84 g (38.4 mmol) N-[3-(trifluoromethyl)phenyl]urea, 5.81 g (38.4 mmol) 4-nitro-benzaldehyde, 5.0 g (38.4 mmol) ethyl 3-oxobutanoate and 15 g polyphosphoric acid ethyl ester are suspended in 100 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 toluene/etiyl 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 toluene/etiyl acetate as eluent

Sources & evidence

ORD record
ord-e7e24b46694742f7a7d4f357563f954f
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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