Hydrochloric Acid → 877133-14-7

HRID 859761Notes

Reaction equation

HRID 859761 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:9]([CH3:10])[N:8]=[C:7]([CH:11]([F:13])[F:12])[N:6]=1)C.Cl>O>[F:13][CH:11]([F:12])[C:7]1[N:6]=[C:5]([CH:4]=[O:3])[N:9]([CH3:10])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58764117HCID 58764117, compound

Product 1

HCID 58764215877133-14-7Yield 56.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Water (190 mL) was added to 5-(diethoxymethyl)-3-(difluoromethyl)-1-methyl-1H-1,2,4-triazole (47.6 g, 0.2024 mol, from Step 2), and the mixture was degassed. Then concentrated HCl (73 mL, 0.81 mol, 11.1 M) was added, and the mixture was stirred at 55–60° C. for 24 h. After this, the reaction mixture was evaporated, and the residue was repeatedly (8–10 times) evaporated with THF until the water and HCl were completely removed. The final residue was distilled under vacuum to give the crude title product (bp 46–50° C. at 0.04 mm Hg), containing, according to LC-MS data, 7% of a dimerization side-product. Further purification on a silica gel (ethyl acetate/hexane 1:3) yielded 18.37 g (56.3%) of 3-(difluoromethyl)-1-methyl-1H-1,2,4-triazole-5-carbaldehyde. Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, CDCl3): δ 4.25 (s, 3H), 6.74 (t, J=56 Hz, 1H), 10.01 (s, 1H). LC/MS (API-ES) calcd for C5H5F2N3O: 161.04, found (M+H+): 162.1; (M+18+H+): 180.1 m/z.

Workup

  1. customthe mixture was degassed
  2. customAfter this, the reaction mixture was evaporated
  3. customevaporated with THF until the water and HCl
  4. customwere completely removed
  5. distillationThe final residue was distilled under vacuum
  6. customto give the crude title product (bp 46–50° C. at 0.04 mm Hg)
  7. additioncontaining
  8. customFurther purification on a silica gel (ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-1db5c5e7969b47d3b9bb4e737047f4b6
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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