Acetic Acid → 2-[5-(Diethoxymethyl)-1-methyl-1H-1,2,4-triazol-3-yl]-6-methylpyridine

HRID 2387134Notes

Reaction equation

HRID 2387134 reaction equation
[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[C:5](=[NH:8])OC)[CH3:2].CN[N:14]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=1)[NH2:16].[C:24](O)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:10]([O:9][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[N:8]([CH3:24])[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=2)[N:14]=1)[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 17874536Methyl 2,2-diethoxyethanecarboximidateHCID 69057285N',6-dimethylpyridine-2-carbohydrazonamide

Product 1

HCID 587642202-[5-(Diethoxymethyl)-1-methyl-1H-1,2,4-triazol-3-yl]-6-methylpyridineYield 57.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 2,2-diethoxyethanimidoate (42 g, 0.26 mol) was dissolved in methanol (200 mL), and a solution of compound N′,6-dimethylpyridine-2-carbohydrazonamide (43 g, 0.25 mol) in methanol (200 mL) while cooling with a water bath, followed by the addition of acetic acid (22 mL, 0.37 mol). The mixture was stirred at room temperature for 3 h, and then K2CO3 (10 g, 0.071 mol) was added. The mixture was stirred for 10 min, and then the methanol was evaporated. The residue was stirred with a solution of K2CO3 (20 g) in water (200 mL), and extracted with ether (2×150 mL). The organic layer was washed with water and then saturated NaCl solution, dried over Na2SO4 and evaporated. The residue (62 g) was purified by chromatography on a silica gel column to afford 39.5 g (57%) of the title product.

Workup

  1. stirringThe mixture was stirred for 10 min
  2. customthe methanol was evaporated
  3. stirringThe residue was stirred with a solution of K2CO3 (20 g) in water (200 mL)
  4. extractionextracted with ether (2×150 mL)
  5. washThe organic layer was washed with water
  6. dry with materialsaturated NaCl solution, dried over Na2SO4
  7. customevaporated
  8. customThe residue (62 g) was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-cec8c495739946e7b2d4617a93dc1476
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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