Acetic Anhydride → 3-(4-Bromo-3,5-dimethyl-phenyl)-5-methyl-[1,2,4]oxadiazole

HRID 237667Notes

Reaction equation

HRID 237667 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[C:18]([CH3:19])=[CH:17][C:12]([C:13]([NH:15]O)=[NH:14])=[CH:11][C:10]=1[CH3:20]>N1C(C)=CC(C)=CC=1C>[Br:8][C:9]1[C:18]([CH3:19])=[CH:17][C:12]([C:13]2[N:14]=[C:5]([CH3:6])[O:7][N:15]=2)=[CH:11][C:10]=1[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178426651HCID 178426651, compound

Product 1

HCID 866973403-(4-Bromo-3,5-dimethyl-phenyl)-5-methyl-[1,2,4]oxadiazole

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

Acetic anhydride (0.35 mL) is added to a solution of 4-bromo-N-hydroxy-3,5-dimethyl-benzamidine (0.30 g) in collidine (3 mL) at room temperature. The solution is stirred at room temperature for 1 h and then at 120° C. for 3 h. After cooling to room temperature, the mixture is concentrated, the residue is taken up in water and acetonitrile, and the resulting mixture is filtered. The filtrate is chromatographed on reversed phase (HPLC; acetonitrile/water/trifluoroacetic acid) to give the title compound. LC (method 11): tR=1.20 min; Mass spectrum (ESI+): m/z=267/269 (Br) [M+H]+.

Workup

  1. waitat 120° C. for 3 h
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture is concentrated
  4. filtrationacetonitrile, and the resulting mixture is filtered
  5. customThe filtrate is chromatographed on reversed phase (HPLC; acetonitrile/water/trifluoroacetic acid)

Sources & evidence

ORD record
ord-8561b8dea9be49b7a965569c1cbfc304
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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