Hydrochloric Acid → HCID 58674240, compound

HRID 2246393Notes

Reaction equation

HRID 2246393 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.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.O=[C:25]([CH3:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].Cl>C1COCC1>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]2[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([CH3:32])[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:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 8868Ethyl AcetoacetateHCID 25712(3-Trifluoromethylphenyl)urea

Product 1

HCID 58674240HCID 58674240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

204 mg (1.0 mmol) N-[3-(trifluoromethyl)phenyl]urea, 108 mg (0.77 mmol) 4-chlorobenzaldehyde and 100 mg (0.77 mmol) ethyl 3-oxobutanoate are suspended in 2 ml of THF, and catalytic amounts of concentrated hydrochloric acid are added. 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-1ef81c48717f49e4bfb2303806463a2a
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

Loading…