Citric Acid → HCID 131720338, compound

HRID 1938637Notes

Reaction equation

HRID 1938637 reaction equation
ClCCCCO[C:7]1([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([Cl:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH2:8]1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29].[I-].[K+].[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38].[OH2:48]>CC(C)=O>[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38].[CH2:28]([N:30]([CH2:31][CH3:32])[CH2:43][CH2:42][CH2:37][CH2:39][O:48][C:10]1[CH:9]=[CH:8][C:7]([C:13]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[Cl:21])=[CH:12][CH:11]=1)[CH3:29]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 962WaterHCID 4875Potassium IodideHCID 8021DiethylamineHCID 86751680HCID 86751680, compound

Product 1

HCID 131720338HCID 131720338, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Combine (E and Z)-1-(4-chlorobutoxy)phenyl-2-chloro-1,2-diphenyl ethylene (20.2 mol), diethylamine (25 L, 241.7 mol), and potassium iodide (3.5 kg, 21.1 mol) in water (15 L). Heat to reflux. After 18 hours, evaporate the reaction mixture in vacuo to give an aqueous residue. Extract two times with ethyl acetate. Evaporate the organic layer in vacuo to give a residue. Combine the residue and acetone (50 L). Add a solution of citric acid (8 kg) in acetone (40 L). Heat to form a solution and cool to give solid. Collect the solid by filtration, rinse with acetone, and dry to give (E and Z)-1-[4-(4-diethylaminobutoxy)phenyl]-1,2-diphenyl-2-chloro-ethylene citrate salt.

Workup

  1. temperatureHeat to reflux
  2. customevaporate the reaction mixture in vacuo
  3. customto give an aqueous residue
  4. extractionExtract two times with ethyl acetate
  5. customEvaporate the organic layer in vacuo
  6. customto give a residue
  7. temperatureHeat
  8. customto form a solution
  9. temperaturecool
  10. customto give solid
  11. customCollect the solid
  12. filtrationby filtration
  13. washrinse with acetone
  14. customdry

Sources & evidence

ORD record
ord-ea16d51e84464d1eb19d8fc263696e10
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

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