Acetic Acid → HCID 178513835, compound

HRID 330443Notes

Reaction equation

HRID 330443 reaction equation
C(O)(=O)C.[O:5]([CH2:12][C:13]1[CH:14]=[C:15]([NH:19][N:20]=[C:21]([C:23]([NH2:25])=[O:24])[NH2:22])[CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]=O>O>[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]1[N:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:14]=2)[N:20]=[C:21]([C:23]([NH2:25])=[O:24])[NH:22]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67970o-FluorobenzaldehydeHCID 54206969HCID 54206969, compound

Product 1

HCID 178513835HCID 178513835, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 15 ml of acetic acid saturated with nitrogen, 2.84 g (0.01 mol) of oxamide 3-(phenoxymethyl)phenylhydrazone was dissolved, and 1.36 g (0.011 mol) of 2-fluorobenzaldehyde was added to the thus formed solution under nitrogen atmosphere and the mixture was stirred for 16 hours at room temperature. After adding water saturated with nitrogen to the mixture, the precipitated crystals were collected by filtration and dried under vacuum. The thus dried crystals were recrystallized from a mixed solvent, saturated with nitrogen, of ethyl acetate and n-hexane to obtain 3.38 g of 5-(2-fluorophenyl)-4,5-dihydro-1-[3-(phenoxymethyl)phenyl]-1H-1,2,4-triazole-3-carboxamide melting at 176°-178° C. in a yield of 86.7%.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customdried under vacuum
  3. customThe thus dried crystals were recrystallized from a mixed solvent, saturated with nitrogen, of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-65aede43314c4b98b3047ca591bdcfac
Source dataset
uspto-grants-1990_01
Patent number
US04897106

Reaction notes

Loading…