Nitric Acid → HCID 12877071, compound

HRID 1154737Notes

Reaction equation

HRID 1154737 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH2:15][CH2:16][CH3:17])=[N:13][C:12]([SH:18])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:19]([O-:22])(O)=[O:20]>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14]([CH2:15][CH2:16][CH3:17])=[N:13][C:12]([S:18][S:18][C:12]3[N:13]=[C:14]([CH2:15][CH2:16][CH3:17])[N:10]([C:7]4[CH:8]=[CH:9][C:4]([N+:19]([O-:22])=[O:20])=[CH:5][CH:6]=4)[N:11]=3)=[N:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178440262HCID 178440262, compound

Product 1

HCID 12877071HCID 12877071, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixure of 35 parts of 1-(4-nitrophenyl)-5-propyl-1H-1,2,4-triazole-3-thiol, 83 parts of concentrated nitric acid solution and 150 parts of water is stirred and warmed to 60° C. While stirring, the mixture is allowed to cool to room temperature and the whole is further stirred overnight at room temperature. The precipitated product is filtered off, washed with water and added to a hot solution of 20 parts of potassium carbonate in 200 parts of water at 100° C. The reaction mixture is allowed to cool to room temperature while stirring. The precipitated product is filtered off, dried and crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and recrystallized from 4-methyl-2-pentanone, yielding 19.8 parts of 3,3'-dithiobis[1-(4-nitrophenyl)-5-propyl-1H-1,2,4-triazole]; mp. 171.5° C.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitated product is filtered off
  3. washwashed with water
  4. additionadded to a hot solution of 20 parts of potassium carbonate in 200 parts of water at 100° C
  5. temperatureto cool to room temperature
  6. stirringwhile stirring
  7. filtrationThe precipitated product is filtered off
  8. customdried
  9. customcrystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  10. filtrationThe product is filtered off
  11. customrecrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-c7674619f1ed43d6b4f1edbc7a417531
Source dataset
uspto-grants-1984_12
Patent number
US04490530

Reaction notes

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