Acetic Acid → 4-[1-(p-Fluorophenyl)-1H-1,2,4-triazol-5-yl]pyridine

HRID 128457

Reaction equation

HRID 128457 reaction equation
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)C.Cl.[F:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1.C(O)(=O)C.[OH-].[Na+]>O.O1CCOCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:6]([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)=[N:5][CH:4]=[N:2]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 12569643N-Dimethylaminomethylene-isonicotinamide

Product 1

HCID 128503004-[1-(p-Fluorophenyl)-1H-1,2,4-triazol-5-yl]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 6.0 g. portion of N-(dimethylaminomethylene)isonicotinamide is added to a mixture prepared by adding 6.05 g. of p-fluorophenylhydrazine hydrochloride to 80 ml. of 30% aqueous acetic acid, 40 ml. of p-dioxane and 7.5 ml. of 5 N sodium hydroxide. The mixture is heated to reflux for 1.5 hours, poured into water and allowed to stand overnight. Extraction with ether gives a dark solid which is recrystallized from acetone-hexane giving 1.7 g. of the desired product, mp. 114°-115° C.

Workup

  1. customprepared
  2. additionby adding 6.05 g
  3. temperatureThe mixture is heated
  4. temperatureto reflux for 1.5 hours
  5. extractionExtraction with ether
  6. customgives a dark solid which
  7. customis recrystallized from acetone-hexane giving 1.7 g

Sources & evidence

ORD record
ord-fa256fbfaab440ac832c11dd4d81f2db
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Linked notes

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