Diethyl Oxalate → HCID 12897298, compound

HRID 1730669Notes

Reaction equation

HRID 1730669 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-60db6b750d5b42a9aadfa901d58ef237
Source dataset
uspto-grants-1976_11
Patent number
US03993679

Reaction notes

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