Citric Acid → HCID 131720265, compound

HRID 2292498Notes

Reaction equation

HRID 2292498 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[Cl:15])=[CH:9][CH:8]=1.[CH2:28]([NH2:30])[CH3:29].[I-].[K+].[C:33]([OH:45])(=[O:44])[CH2:34][C:35]([CH2:40][C:41]([OH:43])=[O:42])([C:37]([OH:39])=[O:38])[OH:36]>CC(=O)CC.CO.ClCCl.O.C(O)C>[C:33]([OH:45])(=[O:44])[CH2:34][C:35]([CH2:40][C:41]([OH:43])=[O:42])([C:37]([OH:39])=[O:38])[OH:36].[CH2:28]([NH:30][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[Cl:15])=[CH:9][CH:8]=1)[CH3:29]

Participants

9

Reactant 4

HCID 311Citric AcidHCID 4875Potassium IodideHCID 6341EthylamineHCID 86749549HCID 86749549, compound

Product 1

HCID 131720265HCID 131720265, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

Combine (E and Z)-1-[4-(4-chlorobutoxy)phenyl]-1,2-diphenyl-2-chloro-ethylene (1.0 g, 2.5 mmol), ethylamine (15 mL, 193 mmol), potassium iodide (0.200 g), ethanol (2 mL), and water (5 mL). Heat to a gentle reflux. After 24 hours, cool to ambient temperature and concentrate in vacuo to obtain a residue. Chromatograph on silica gel eluting with 7% methanol/dichloromethane to obtain a residue. Combine the residue and butanone (6 mL). Add citric acid (0.52 g, 2.7 mmol) dissolved in butanone (4 mL). Allow to slowly evaporate until a solid forms, filter, and dry in vacuo to give the title compound.

Workup

  1. temperatureHeat to a gentle reflux
  2. concentrationconcentrate in vacuo
  3. customto obtain a residue
  4. customto slowly evaporate until a solid forms
  5. filtrationfilter
  6. customdry in vacuo

Sources & evidence

ORD record
ord-f756536ef2b5471c8c6913ec38196487
Source dataset
uspto-grants-1997_11
Patent number
US05684004

Reaction notes

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