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Hydrochloric Acid → 3,3'-Dinitro-4,4'-di-2-furoylaminobiphenyl

HRID 49748
Notes
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Reaction equation

HRID 49748 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[NH2:10])([O-:3])=[O:2].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](Cl)=[O:27].Cl>O.N1C=CC=CC=1.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:26]([C:22]3[O:21][CH:25]=[CH:24][CH:23]=3)=[O:27])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[NH:10][C:26]([C:22]1[O:21][CH:25]=[CH:24][CH:23]=1)=[O:27])([O-:3])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 682422-Furancarbonyl chlorideHCID 31067203,3'-Dinitrobenzidine

Product 1

HCID 227415993,3'-Dinitro-4,4'-di-2-furoylaminobiphenylYield 81.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×
HCID 1049
Pyridine
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
8.5 °C

Procedure

In a 500 ml separable flask equipped with a stirrer, a reflux condenser cooled with water, a thermometer and a dropping funnel, 10.96 g of 3,3′-dinitro-4,4′-diaminobiphenyl was dissolved into 200 ml of N,N-dimethylformamide and then 20 ml of pyridine was added to the solution. While the prepared solution was cooled at 3 to 14° C., 12.53 g of 2-furoyl chloride was added dropwise to the solution. After the addition was completed, the reaction solution was warmed to the room temperature and stirred for further 5 hours. Then, 80 ml of 2N hydrochloric acid and 100 ml of water were added to the solution and the solid substance was separated by filtration. The obtained solid substance was washed well with water and dried in a reduced pressure to obtain 15.0 g of 3,3′-dinitro-4,4′-di-2-furoylamino-biphenyl. The yield was 81%.

Workup

  1. customIn a 500 ml separable flask equipped with a stirrer, a reflux condenser
  2. additionAfter the addition
  3. temperaturethe reaction solution was warmed to the room temperature
  4. customthe solid substance was separated by filtration
  5. washThe obtained solid substance was washed well with water
  6. customdried in a reduced pressure

Sources & evidence

ORD record
ord-7025cbae4e164e20a9fa5ffa430be656
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06709804B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes