Water → HCID 20156384, compound

HRID 986814Notes

Reaction equation

HRID 986814 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18].O>N1C=CC=CC=1>[NH2:11][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=1[NH:10][C:17]([C:13]1[O:12][CH:16]=[CH:15][CH:14]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 682422-Furancarbonyl chlorideHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 20156384HCID 20156384, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 4-nitro-o-phenylene diamine (76.5 g, 0.5 mole) in 500 ml of pyridine, is added dropwise 2-furoyl chloride (65 g, 0.5 mole). After the addition is complete the reaction solution is stirred at room temperature for 15 minutes and then at reflux for 2 hr. The hot reaction solution is poured into 6 liters of water to give an oil, which solidifies upon standing overnight at room temperature to give 125 g (100 percent) of yellow intermediate. The solid is used in part B without further purification.

Workup

  1. additionAfter the addition
  2. temperatureat reflux for 2 hr
  3. customto give an oil, which
  4. waitupon standing overnight at room temperature

Sources & evidence

ORD record
ord-7de4eb6d726c49f781fa027529affb33
Source dataset
uspto-grants-1987_12
Patent number
US04716168

Reaction notes

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