Ethanol → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde-ethylsemicarbazone

HRID 241515Notes

Reaction equation

HRID 241515 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[CH2:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17](C=O)=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[CH2:28]([NH:30][NH:31][C:32]([NH2:34])=[O:33])C.[CH2:35](O)[CH3:36]>C(O)(=O)C>[CH2:35]([N:31]([C:32]([NH2:34])=[O:33])[N:30]=[CH:28][C:17]1[CH:20]=[CH:21][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:23]([F:25])([F:24])[F:26])[CH2:13][N:12]=2)=[CH:15][C:16]=1[CH3:22])[CH3:36]

Participants

5

Reactant 3

HCID 702EthanolHCID 86690409Ethyl semicarbazide hydrochlorideHCID 866910474-[3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-2-methyl-benzaldehyde

Product 1

HCID 668367384-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde-ethylsemicarbazoneYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzaldehyde (208 mg, 0.520 mmol) and ethyl semicarbazide hydrochloride (109 mg 0.780 mmol) in ethanol (5 mL) and glacial acetic acid (0.1 mL) was heated at 70° C. for 4 h. After cooling, the mixture was concentrated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (151 mg, 60%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuum
  3. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-322d62e1edea4388a836c312a79de4a0
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Reaction notes

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