Acetic Anhydride → 3-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid

HRID 330793Notes

Reaction equation

HRID 330793 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])=[NH:4].[C:14](OC(=O)C)(=O)[CH3:15]>C(O)(=O)C>[CH3:14][C:15]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])[N:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178513298HCID 178513298, compound

Product 1

HCID 71278183-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
118 °C

Procedure

A mixture of 614 g (3.41 mol) of 3-(N-hydroxycarbamimidoyl)benzoic acid, 756 ml (8.0 mol) of acetic anhydride and 2 l of acetic acid is heated at a temperature of 118° C. for 14 hours. The reaction mixture is cooled to 6° C. and filtered off with suction. The residue is taken up in 2 l of water, filtered off with suction and washed well with water. The residue is recrystallised from ethanol/water: 3-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic acid as colourless crystals; m.p. 225°; ESI 205 (M+H).

Workup

  1. temperatureThe reaction mixture is cooled to 6° C.
  2. filtrationfiltered off with suction
  3. filtrationfiltered off with suction
  4. washwashed well with water
  5. customThe residue is recrystallised from ethanol/water

Sources & evidence

ORD record
ord-3a4dc34c0aa1491689ac359a7df09a73
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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