Triethylamine → 5-[4-nitrophenyl]-4-(4-methoxyphenyl)-methyl-4H-1,2,4-triazol-3-methanol

HRID 1197872Notes

Reaction equation

HRID 1197872 reaction equation
C(N(CC)CC)C.[C:8]([NH:13][NH2:14])(=O)[CH:9]([CH3:11])[OH:10].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=O)[C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[N+:31]([C:28]1[CH:29]=[CH:30][C:25]([C:24]2[N:23]([C:20]3[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)[C:8]([CH:9]([CH3:11])[OH:10])=[N:13][N:14]=2)=[CH:26][CH:27]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3120432-HydroxypropanehydrazideHCID 532159N-(4-methoxyphenyl)-4-nitrobenzamide

Product 1

HCID 136334335-[4-nitrophenyl]-4-(4-methoxyphenyl)-methyl-4H-1,2,4-triazol-3-methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3 ml of triethylamine were added at ambient temperature to a solution of 2 equivalents of -lactic acid hydrazide in 60 ml of toluene and then, 4.3 g of N-(4-methoxyphenyl)-4-nitrobenzene carboximidoyl chloride (Step A of Example 1) were added in two lots with stirring for 4 hours at ambient temperature. The mixture was then refluxed for 4 hours to obtain cyclization and the toluene was eliminated under reduced pressure. After washing with water, filtering and drying, 4.34 g of crude product were obtained which was purified by chromatography under pressure (eluent-chloroform-ethyl acetate-methanol: 47:50:3) to obtain 3 g of 5-[4-nitrophenyl]-4-(4-methoxyphenyl)-methyl-4H-1,2,4-triazol-3-methanol melting at 140° C.

Workup

  1. temperatureThe mixture was then refluxed for 4 hours
  2. customto obtain cyclization
  3. washAfter washing with water
  4. filtrationfiltering
  5. customdrying
  6. custom4.34 g of crude product were obtained which
  7. customwas purified by chromatography under pressure (eluent-chloroform-ethyl acetate-methanol: 47:50:3)

Sources & evidence

ORD record
ord-8fd058e84ad8481291a98f5800c7cc75
Source dataset
uspto-grants-1994_01
Patent number
US05278180

Reaction notes

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