Hydrochloric Acid → HCID 58764168, compound

HRID 2387160Notes

Reaction equation

HRID 2387160 reaction equation
Cl.C([O:4][CH:5](OCC)[C:6]1[N:10]=[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)[N:8]([CH3:17])[N:7]=1)C.C(=O)([O-])[O-].[K+].[K+]>>[CH3:17][N:8]1[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[N:10][C:6]([CH:5]=[O:4])=[N:7]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58764202HCID 58764202, compound

Product 1

HCID 58764168HCID 58764168, compoundYield 94.6%

Procedure

To a 4 N solution of HCl (185 mL, 0.74 mol) was added 3-(diethoxymethyl)-1-methyl-5-(1-methyl-1H-pyrazol-5-yl)-1H-1,2,4-triazole (40.1 g, 0.151 mol), and the reaction mixture was left to stir overnight. To the resulting mixture was added potassium carbonate (166 g) in portions under vigorous stirring, and the resulting mixture was extracted with ethyl acetate (5×300 mL). The organic layer was dried with anhydrous sodium sulfate, and the solvents were removed under vacuum on a rotary evaporator. To the residue was added absolute ether (4×100 mL) to give 27.3 g (94.5%) of the title product as a light-beige powder. Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, DMSO-d6): δ 4.04 (s, 3H), 4.08 (s, 3H), 6.98 (d, J=2 Hz, 1H), 7.67 (d, J=2 Hz, 1H), 9.95 (s, 1H). LC/MS (API-ES) calcd for C8H9N5O: 191.08, found (M+H+): 192.0 m/z.

Workup

  1. waitthe reaction mixture was left
  2. extractionthe resulting mixture was extracted with ethyl acetate (5×300 mL)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. customthe solvents were removed under vacuum on a rotary evaporator
  5. additionTo the residue was added absolute ether (4×100 mL)

Sources & evidence

ORD record
ord-65636255e0c84773baf09212a0259314
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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