N-Phenyl-o-phenylenediamine → HCID 12374327, compound

HRID 1415102Notes

Reaction equation

HRID 1415102 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:16]([CH2:21][C:22](=N)O)([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH2:19]([O:18][C:16]([CH2:21][C:22]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 68297N-Phenyl-o-phenylenediamineHCID 178472149HCID 178472149, compound

Product 1

HCID 12374327HCID 12374327, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-phenyl-o-phenylenediamine (55.27g; 0.3 mole) and carboethoxyacetimidate hydrochloride [Ber., 28, 478 (1895)](58.70g; 0.3 mole) are refluxed in ethanol (200ml) for 4 hours. The separated ammonium chloride is filtered from the hot solution. The filtrate is evaporated to a syrup which is taken up in chloroform and washed twice with water. After drying (MgSO4), the chloroform is evaporated, ligroin is added, and crystallization slowly occurs. The solid is filtered and recrystallized from ligroine to give 50.3g (59.8%); m.p. 87°-89°; Lit. m.p. 89°-91° [J. Hetero. Chem., 3(3), 280 (1966)].

Workup

  1. filtrationThe separated ammonium chloride is filtered from the hot solution
  2. customThe filtrate is evaporated to a syrup which
  3. washwashed twice with water
  4. dry with materialAfter drying (MgSO4)
  5. customthe chloroform is evaporated
  6. additionligroin is added
  7. customcrystallization
  8. filtrationThe solid is filtered
  9. customrecrystallized from ligroine
  10. customto give 50.3g (59.8%)

Sources & evidence

ORD record
ord-01c9210235924ee2831d8a3f81e7d4c6
Source dataset
uspto-grants-1977_01
Patent number
US04003750

Reaction notes

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