HCID 13054017, compound → HCID 13174852, compound

HRID 4598Notes

Reaction equation

HRID 4598 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1)[CH3:2]>Cl>[CH2:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 13054017HCID 13054017, compound

Product 1

HCID 13174852HCID 13174852, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A solution of 23 g of stannous chloride in 20 ml of concentrated hydrochloric acid was added all at once to a solution of 10 g of 3-ethyl-5-(4-methoxyphenyl)-4-(4-nitrophenyl)-4H-1,2,4-triazole in 50 ml of concentrated hydrochloric acid and the mixture was vigorously stirred for 2 hours and was filtered. The recovered product was washed with N hydrochloric acid and was added to aqueous 5N sodium hydroxide solution. The mixture was stirred for 2 hours and was filtered and the white crystals were washed and dried at 110° C. under reduced pressure. The 12.5 g of crystals were dissolved in boiling toluene and the mixture was filtered. The filtrate was iced for 16 hours and was vacuum filtered. The product was dried to obtain 3.8 g of 4-[3-ethyl-5-(4-methoxyphenyl)-4H-1,2,4-triazol-4-yl]-benzeneamine in the form of crystals melting at 216° C.

Workup

  1. filtrationwas filtered
  2. washThe recovered product was washed with N hydrochloric acid
  3. additionwas added to aqueous 5N sodium hydroxide solution
  4. stirringThe mixture was stirred for 2 hours
  5. filtrationwas filtered
  6. washthe white crystals were washed
  7. customdried at 110° C. under reduced pressure
  8. dissolutionThe 12.5 g of crystals were dissolved
  9. filtrationthe mixture was filtered
  10. waitThe filtrate was iced for 16 hours
  11. filtrationfiltered
  12. customThe product was dried

Sources & evidence

ORD record
ord-118d97fa6ea14796a1c2c555fbaee88f
Source dataset
uspto-grants-1988_02
Patent number
US04727084

Reaction notes

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