Methanol → Methyl 3-(5-methyl-1,2,4-oxadiazol-3-YL)benzoate

HRID 1970873Notes

Reaction equation

HRID 1970873 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])[N:8]=1.O.[CH3:22]O>>[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([O:17][CH3:22])=[O:16])[N:8]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 71278183-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 53429639Methyl 3-(5-methyl-1,2,4-oxadiazol-3-YL)benzoate

Procedure

7.83 ml (147 mmol) of concentrated sulfuric acid are added to a suspension of 30.0 g (147 mmol) of 3-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic acid in 150 ml of methanol, and the mixture is heated at the boil for 18 hours. The reaction mixture is cooled in an ice bath, water is added, and the solid is filtered off with suction and washed well with water:methyl 3-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate as colourless crystals; m.p. 81° C.; ESI 219 (M+H); HPLC: Rt=2.65 min (method B).

Workup

  1. temperaturethe mixture is heated at the boil for 18 hours
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. filtrationthe solid is filtered off with suction
  4. washwashed well with water

Sources & evidence

ORD record
ord-237a5a3299c44a039fa44390461c8d63
Source dataset
uspto-grants-2013_04
Patent number
US08431572B2

Reaction notes

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