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

HRID 330794Notes

Reaction equation

HRID 330794 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, the mixture 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 A).

Workup

  1. temperaturethe mixture is heated at the boil for 18 hours
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. filtrationthe mixture is filtered off with suction
  4. washwashed well with water
  5. custom=2.65 min (method A)

Sources & evidence

ORD record
ord-9e97ec0013794d7495789bd38f7c513f
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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