Ammonia → 1-(4-Amino-3-cyano-5-methylphenyl)-1,2,4-triazole

HRID 2231658Notes

Reaction equation

HRID 2231658 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:4][C:3]=1I.N.[CH3:16][N:17]1CCCC1=O>>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:4][C:3]=1[C:16]#[N:17]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 212855261-(4-Amino-3-iodo-5-methyl-phenyl)-1,2,4-triazole

Product 1

HCID 212855321-(4-Amino-3-cyano-5-methylphenyl)-1,2,4-triazole

Procedure

A mixture of 1-(4-amino-3-iodo-5-methyl-phenyl)-1,2,4-triazole (14.23 g) and cuprous cyanide (5.94 g) was heated at 120° in N-methylpyrrolidone (32 cm3) for 2.5 hours. The cooled mixture was poured into ammonia solution (100 cm3 ; S.G. 0.880) and the resulting solution was extracted with chloroform:methanol, 19:1 (3×150 cm3). The combined and dried (MgSO4) organic extracts were filtered and evaporated in vacuo (0.5 mm) to afford an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate:methanol, 19:1. Combination and evaporation of appropriate fractions gave an oil which crystallised on trituration with ether to give the title compound, m.p. 231°-3° (2.8 g).

Workup

  1. extractionthe resulting solution was extracted with chloroform
  2. dry with materialdried (MgSO4) organic extracts
  3. filtrationwere filtered
  4. customevaporated in vacuo (0.5 mm)
  5. customto afford an oil which
  6. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  7. washeluting with ethyl acetate
  8. customCombination and evaporation of appropriate fractions
  9. customgave an oil which
  10. customcrystallised on trituration with ether

Sources & evidence

ORD record
ord-81e6d15689bc40278ff1a5f4b7d8c09a
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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