Ethanol → [(5-Chloro-2-hydroxy-alpha-phenylbenzyliden)amino] malonic acid diethyl ester

HRID 66243Notes

Reaction equation

HRID 66243 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[C:7](=[NH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)C.Cl.[CH2:21]([O:23][C:24](=[O:32])[CH:25](N)[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:22]>N1C=CC=CC=1>[CH2:21]([O:23][C:24](=[O:32])[CH:25]([N:14]=[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]1[CH:15]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:16])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)HCID 1357053525-Chloro-2-hydroxy-benzophenone imine

Product 1

HCID 136388409[(5-Chloro-2-hydroxy-alpha-phenylbenzyliden)amino] malonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 9.2 g. of 5-chloro-2-hydroxy-benzophenone imine in 60 ml. of ethanol is treated with 12.6 g. of aminomalonic acid diethyl ester hydrochloride and 5.0 ml. of pyridine and the mixture boiled at reflux for 1 hour while stirring. The mixture is then concentrated to dryness under reduced pressure and the residue partitioned between toluene and water. The organic phase is washed with water, briefly dried over sodium sulfate and evaporated to dryness. The residual oily residue crystallizes upon trituration with hexane. There is obtained [(5-chloro-2-hydroxy-α-phenylbenzyliden)amino] malonic acid diethyl ester, having a melting point of 55°-56° C. Recrystallization from ethanol yields gold-yellowish leaflets having the same melting point.

Workup

  1. additionA suspension of 9.2 g
  2. temperatureat reflux for 1 hour
  3. concentrationThe mixture is then concentrated to dryness under reduced pressure
  4. customthe residue partitioned between toluene and water
  5. washThe organic phase is washed with water
  6. dry with materialbriefly dried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residual oily residue crystallizes upon trituration with hexane

Sources & evidence

ORD record
ord-8a3c4183e8df4165b52cc1487f2a57a7
Source dataset
uspto-grants-1978_12
Patent number
US04130717

Reaction notes

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