Methanol → HCID 178499187, compound

HRID 923320Notes

Reaction equation

HRID 923320 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([OH:9])=[O:8])[N:3]=1.O=S(Cl)Cl.[CH3:14]O>>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH3:14])=[O:8])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178508560HCID 178508560, compound

Product 1

HCID 178499187HCID 178499187, compoundYield 65%

Conditions

Temperature
70 °C

Procedure

To a solution of 5-amino-1H-1,2,4-triazole-3-carboxylic acid (3.9 g, 30.45 mmol) in methanol (100 ml) was added SOCl2 (12 g, 100.84 mmol). The resulting solution was stirred for 48 h at 70° C. The resulting mixture was concentrated under vacuum, dissolved in water (100 ml), the pH was adjusted to 8 with NaHCO3 solution, and then extracted with dichloromethane (3×50 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated under vacuum to afford methyl 5-amino-1H-1,2,4-triazole-3-carboxylate as a white solid (800 mg, 65%).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. dissolutiondissolved in water (100 ml)
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-de2d707b62a742d5a97dc35301d94b59
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

Loading…