Hydrochloric Acid → HCID 54339727, compound

HRID 1413922Notes

Reaction equation

HRID 1413922 reaction equation
[N+:1]([C:4]1[CH:39]=[CH:38][C:7]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[O:17][C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][C:29]5[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=5)=[CH:23][CH:22]=4)=[N:19][N:20]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.CN(C)C=O.Cl.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].O>[NH2:35][C:32]1[CH:31]=[CH:30][C:29]([CH:28]=[CH:27][C:24]2[CH:23]=[CH:22][C:21]([C:18]3[O:17][C:16]([C:13]4[CH:14]=[CH:15][C:10]([CH:9]=[CH:8][C:7]5[CH:38]=[CH:39][C:4]([NH2:1])=[CH:5][CH:6]=5)=[CH:11][CH:12]=4)=[N:20][N:19]=3)=[CH:26][CH:25]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 538881352,5-Bis{4-[2-(4-nitrophenyl)ethenyl]phenyl}-1,3,4-oxadiazole

Product 1

HCID 54339727HCID 54339727, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

After mixing 6.0 g of 2,5-bis[4-(p-nitrostyryl)phenyl]-1,3,4-oxadiazole, 12.0 g of iron powder and 200 g of N,N-dimethyl formamide together, by adding dilute hydrochloric acid prepared by employing 5 ml of undiluted hydrochloric acid and 17 ml of water to the resulting mixture and intensely stirring it, reaction was effected at a temperature of 90° to 100° C. for one hour. After completing the reaction, by adding a 5% aqueous solution of sodium carbonate while heating as above, the pH value of the reactant mixture was adjusted to be 8, the undissolved matter was filtered while heating, and the resulting filtrate was diluted with 70 ml of water, whereby there were separated yellow crystals. Then, said crystals were collected by filtering, washed in water and dried, whereby there were obtained 5.0 g (yield rate: 94.3%) of 2,5-bis[4-(p-aminostyryl)phenyl]-1,3,4-oxadiazole. The melting point of this crystal was 250° C. or more (decomposition point).

Workup

  1. customprepared
  2. customit, reaction
  3. customthe reaction
  4. temperaturewhile heating as above, the pH value of the reactant mixture
  5. filtrationthe undissolved matter was filtered
  6. temperaturewhile heating
  7. additionthe resulting filtrate was diluted with 70 ml of water, whereby there
  8. customwere separated yellow crystals
  9. customwere collected
  10. filtrationby filtering
  11. washwashed in water
  12. customdried

Sources & evidence

ORD record
ord-230eca3e06854635ae84eacd4b7c9e6b
Source dataset
uspto-grants-1981_02
Patent number
US04251613

Reaction notes

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