Acetic Acid → Pyridine, 3-(2-methyl-2H-1,2,3-triazol-4-yl)-

HRID 1600445Notes

Reaction equation

HRID 1600445 reaction equation
[N+:1](=[CH2:3])=[N-:2].[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=NN[CH:14]=2)[CH:5]=1.C(O)(=O)C.C(OCC)(=O)C>CCOCC.C(O)C>[CH3:3][N:1]1[N:11]=[C:10]([C:6]2[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=2)[CH:14]=[N:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 9550DiazomethaneHCID 178420773HCID 178420773, compound

Product 1

HCID 10441962Pyridine, 3-(2-methyl-2H-1,2,3-triazol-4-yl)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of ca. 3.0 g (0.070 mol) diazomethane in ether was added dropwise to a solution of 6.0 g (0.04 mol) of 68 in 150 ml of ethanol at room temperature. The solution was stirred overnight at ambient temperature. Ca. 1 ml of acetic acid was added and the mixture was evaporated in vacuo. Water (75 ml) was added and the solution made basic with ammonia. Extraction with 3×100 ml of ether, drying of the organic phase over magnesium sulphate, and removal of the solvent in vacuo gave a brown solid which as applied to a silica gel column (eluent: ethyl acetate) giving a colorless solid, 69. Yield: 2.8 g (0.018 mol, 43%).

Workup

  1. customthe mixture was evaporated in vacuo
  2. additionWater (75 ml) was added
  3. extractionExtraction with 3×100 ml of ether
  4. dry with materialdrying of the organic phase over magnesium sulphate, and removal of the solvent in vacuo
  5. customgave a brown solid which
  6. customgiving a colorless solid, 69

Sources & evidence

ORD record
ord-d0fd52035f454e118ab995b215846694
Source dataset
uspto-grants-1999_11
Patent number
USRE036374

Reaction notes

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