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1-Chloro-4-nitrobenzene → HCID 178507292, compound

HRID 1197401
Notes
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Reaction equation

HRID 1197401 reaction equation
[NH2:1][C:2]1[S:3][C:4]([NH2:7])=[CH:5][CH:6]=1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14](Cl)=[CH:13][CH:12]=1)([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C)C=O>[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:6]2[CH:5]=[C:4]([NH2:7])[SH:3]([C:14]3[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=3)([C:14]3[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=3)([C:14]3[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=3)[C:2]=2[NH2:1])=[CH:13][CH:12]=1)([O-:10])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 19599071Thiophene-2,5-diamine

Product 1

HCID 178507292HCID 178507292, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228
Dimethylformamide
Solvent

Procedure

In 600 parts of dimethylformamide, 0.5 mol (60 parts) of 2,5-diaminothiophene, 2.3 mol (360 parts) of p-nitrochlorobenzene, 1.2 mol (170 parts) of anhydrous potassium carbonate and 10 parts of copper powder were refluxed with stirring for 4 days. After the reaction was completed, the reaction mixture was filtered, and the residue was thoroughly washed with dimethylformamide, water and acetone, and then dried. Thus, 105 parts of reddish brown tetrakis(p-nitrophenyl)-2,5-diaminothiophene was obtained.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe residue was thoroughly washed with dimethylformamide, water and acetone
  3. customdried

Sources & evidence

ORD record
ord-eb3176188d074544b1de8a676f3e6622
Source dataset
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05275925

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes