2-Nitropropane → HCID 23465182, compound

HRID 443724Notes

Reaction equation

HRID 443724 reaction equation
[Na].[N+](C(C)C)([O-])=[O:3].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[N:20]=[C:19]([C:21]#[N:22])[CH:18]=[N:17]2)=[CH:12][CH:11]=1>C(O)C>[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[N:20]=[C:19]([C:21]#[N:22])[CH:18]=[N:17]2)=[CH:12][CH:11]=1)=[O:3]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 23465190HCID 23465190, compound

Product 1

HCID 23465182HCID 23465182, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.6 g of sodium are dissolved in 300 ml of absolute ethanol, with stirring and whilst passing a vigorous stream of nitrogen over the mixture. 23.2 g of 2-nitropropane (purity: about 95%) are then added dropwise at 21° C. in the course of 5 minutes and the reaction mixture is stirred at 20° to 25° C. for a further 2 hours. 52.6 g of 2-(p-bromomethyl-phenyl)-4-cyano-2H-1,2,3-triazole are then introduced and the reaction mixture is slowly heated up to the reflux temperature and refluxed for 2 hours. After cooling, the product which has crystallised out is filtered off with suction, stirred with 500 ml of water, again filtered off with suction and washed well with about 2 liters of water. This gives 21.8 g of 2-(p-formyl-phenyl)-4-cyano-2H-1,2,3-triazole with a melting point of 148° to 150° C.

Workup

  1. stirringthe reaction mixture is stirred at 20° to 25° C. for a further 2 hours
  2. temperaturethe reaction mixture is slowly heated up to the reflux temperature
  3. temperaturerefluxed for 2 hours
  4. temperatureAfter cooling
  5. customthe product which has crystallised out
  6. filtrationis filtered off with suction
  7. stirringstirred with 500 ml of water
  8. filtrationagain filtered off with suction
  9. washwashed well with about 2 liters of water

Sources & evidence

ORD record
ord-87e20ea3bd364f3486f4f3b4f2647de5
Source dataset
uspto-grants-1981_04
Patent number
US04261855

Reaction notes

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