Acetic Acid → Methyl (5-phenyl-1H-1,2,4-triazol-1-yl)acetate

HRID 1742015Notes

Reaction equation

HRID 1742015 reaction equation
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.Cl.[C:15]([OH:18])(=[O:17])C.[CH3:19][NH:20]N.[C:22](O)(=O)C>>[C:7]1([C:6]2[N:20]([CH2:19][C:15]([O:18][CH3:22])=[O:17])[N:2]=[CH:4][N:5]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4309686N-[(1E)-(Dimethylamino)methylene]benzamideHCID 86748058HCID 86748058, compound

Product 1

HCID 53935479Methyl (5-phenyl-1H-1,2,4-triazol-1-yl)acetateYield 96%

Procedure

N-[(Dimethylamino)methylene]benzamide (2.0 g, 0.011 mol) and methyl hydrazine acetate hydrochloride salt (1.9 g, 0.011 mol) were warmed in acetic acid at 90° C. for 11/2 hours. The acetic acid was evaporated under reduced pressure and the residue neutralised with saturated aqueous sodium bicarbonate, then extracted into chloroform (2×100 ml) washed with water, dried and evaporated under reduced pressure to give methyl [5-phenyl-1,2,4-triazol-1-yl]acetate as a clear oil (2.3 g, 96%).

Workup

  1. customThe acetic acid was evaporated under reduced pressure
  2. extractionextracted into chloroform (2×100 ml)
  3. washwashed with water
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d8ee907f21fe4f728b6f80ad1952d633
Source dataset
uspto-grants-1994_08
Patent number
US05336682

Reaction notes

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