Acetic Acid → HCID 20160800, compound

HRID 247432Notes

Reaction equation

HRID 247432 reaction equation
[C:1]([C:4](=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[C:5]([O:7]CCC#N)=[O:6])(=O)[CH3:2].[NH2:22]/[C:23](/[CH3:49])=[CH:24]\[C:25]([O:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][C:34]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:33][CH2:32]1)=[O:26].C(O)(=O)C>CC(O)C>[C:43]1([C:34]2([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:33][CH2:32][N:31]([CH2:30][CH2:29][CH2:28][O:27][C:25]([C:24]3[CH:12]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=4)[C:4]([C:5]([OH:7])=[O:6])=[C:1]([CH3:2])[NH:22][C:23]=3[CH3:49])=[O:26])[CH2:36][CH2:35]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 54455193HCID 54455193, compoundHCID 67836697HCID 67836697, compound

Product 1

HCID 20160800HCID 20160800, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

8.1 g of 2-cyanoethyl 2-acetyl-3-(3-nitrophenyl)acrylate and 10.6 g of 3-(4,4-diphenylpiperid-1-yl)-propyl 3-aminocrotonate are heated at the boiling point under reflux in 120 ml of 2-propanol and 0.5 ml of glacial acetic acid for 4 hours. After most of the solvent has been distilled off and 2 portions of 50 ml of toluene each have been added, the residue is concentrated to dryness. The residue, which has foamed as a solid, is taken up in isopropanol, and diethyl ether is added to the clear solution until the resulting cloudiness first persists. After the mixture has been left to stand in a refrigerator, the starting compound crystallizes out in the form of fine platelets. m.p.: 158°-160° C.; yield: 14.3 g.

Workup

  1. distillationAfter most of the solvent has been distilled off
  2. addition2 portions of 50 ml of toluene each have been added
  3. concentrationthe residue is concentrated to dryness
  4. additiondiethyl ether is added to the clear solution until the resulting cloudiness
  5. waitAfter the mixture has been left
  6. customthe starting compound crystallizes out in the form of fine platelets

Sources & evidence

ORD record
ord-1c38e978d1a0479c99127cfb93295a1d
Source dataset
uspto-grants-1987_11
Patent number
US04707486

Reaction notes

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