Hydrochloric Acid → HCID 53710909, compound

HRID 1733409Notes

Reaction equation

HRID 1733409 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.Cl.O.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)=[CH:12][CH:11]=2)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 544698941,1'-[1,4-Phenylenedi(ethene-2,1-diyl)]bis(4-nitrobenzene)

Product 1

HCID 53710909HCID 53710909, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6228DimethylformamideSolvent

Procedure

25.9 g of 1,4-bis(4-nitrostyryl)benzene were added to a mixture consisting of 50 g of iron powder, 12 ml of undiluted hydrochloric acid, 50 ml of water and 800 ml of N,N-dimethyl formamide and subjected to 1.5 hours' intense stirring at a temperature in the range of from 90° to 100° C. Thereafter, the pH value was adjusted to be 8 by means of 10% aqueous solution of sodium carbonate while thus heating, and the undissolved matter was filtered. From the resulting filtrate were separated yellow crystals, and these crystals were collected by filtering, washed in water, dried, and thereafter recrystallized from N,N-dimethyl formaldehyde, whereby there were obtained 20.9 g (yield rate: 95.7%) of 1,4-bis(4-aminostyryl)benzene in the form of yellow crystals (melting point: 300° C. or more).

Workup

  1. temperaturewhile thus heating
  2. filtrationthe undissolved matter was filtered
  3. customFrom the resulting filtrate were separated yellow crystals
  4. customthese crystals were collected
  5. filtrationby filtering
  6. washwashed in water
  7. customdried
  8. customrecrystallized from N,N-dimethyl formaldehyde

Sources & evidence

ORD record
ord-bd4a35b4a81046acbf8b0f820768eb7c
Source dataset
uspto-grants-1980_12
Patent number
US04242260

Reaction notes

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