Hydrochloric Acid → HCID 59218319, compound

HRID 2246388Notes

Reaction equation

HRID 2246388 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].O=[C:23]([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].Cl>C1COCC1>[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([CH3:30])[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:9](=[O:10])[NH:11]2)=[CH:16][CH:15]=1)#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 160753-ChlorophenylureaHCID 660424-Cyanobenzaldehyde

Product 1

HCID 59218319HCID 59218319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

170 mg (1.0 mmol) N-[3-chlorophenyl]urea, 100 mg (0.77 mmol) 4-cyanobenzaldehyde 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-6a7b3688841d4acd883d18a186a6c2e2
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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