Hydrochloric Acid → 3-(3-Fluorophenyl)-1-methyl-1H-1,2,4-triazole-5-carbaldehyde hydrochloride dihydrate

HRID 2387156Notes

Reaction equation

HRID 2387156 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[N:6]=1)C.[ClH:21]>>[OH2:3].[OH2:3].[ClH:21].[F:17][C:13]1[CH:12]=[C:11]([C:7]2[N:6]=[C:5]([CH:4]=[O:3])[N:9]([CH3:10])[N:8]=2)[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 587642595-(Diethoxymethyl)-3-(3-fluorophenyl)-1-methyl-1H-1,2,4-triazole

Product 1

HCID 866053753-(3-Fluorophenyl)-1-methyl-1H-1,2,4-triazole-5-carbaldehyde hydrochloride dihydrateYield 47%

Procedure

A solution of 5-(diethoxymethyl)-3-(3-fluorophenyl)-1-methyl-1H-1,2,4-triazole (24.0 g, 86 mmol) in 4M HCl (86 mL) was stirred at 60° C. for 2 h. The mixture was concentrated in vacuo, and the residue was recrystallized from MeOH/Et2O mixture (1:1). The resulting solvate was dissolved in water/THF (1:2) and concentrated in vacuo to dryness to afford 11.33 g (47%) of the title product. Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, D2O+TFA): δ 4.16 (s, 3H), 6.47 (s, 1H), 7.42 (m, 1H), 7.62 (m, 1H), 7.70 (m, 1H), 7.77 (m, 1H). LC/MS (API-ES) calcd for C10H8FN3O: 205.07, found (M+H+): 206.0; (M+18+H+): 224.0 m/z.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was recrystallized from MeOH/Et2O mixture (1:1)
  3. dissolutionThe resulting solvate was dissolved in water/THF (1:2)
  4. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-1cd4a6991def40d5a33a0edcd183d8d1
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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