Diethyl Oxalate → HCID 12897298, compound

HRID 236926Notes

Reaction equation

HRID 236926 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[C:9]([O:16][CH2:17][CH3:18])(=[O:15])[C:10]([O:12]CC)=O>CCOCC>[C:1]1([NH:8][C:10](=[O:12])[C:9]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:10](=[O:12])[C:9]([O:16][CH2:17][CH3:18])=[O:15])[CH:2]=1

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 7935M-Phenylenediamine

Product 1

HCID 12897298HCID 12897298, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of m-phenylenediamine (10.8 grams) 0.10 ml.) and diethyl oxalate (50 ml.) is refluxed for 2.5 hours. The cooled reaction mixture is diluted with ether (200 ml.) and the crude product collected (19.2 grams, M.P. 150° C.). Two recrystallizations from methanol give off white crystals (6.65 grams, 155°-160°).

Workup

  1. customThe cooled reaction mixture
  2. customthe crude product collected (19.2 grams, M.P. 150° C.)
  3. customTwo recrystallizations from methanol
  4. customgive off white crystals (6.65 grams, 155°-160°)

Sources & evidence

ORD record
ord-a4481143b14f4c7eaa14673a4fb60119
Source dataset
uspto-grants-1979_06
Patent number
US04159278

Reaction notes

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