Trimethylorthoacetate → HCID 82481670, compound

HRID 538098Notes

Reaction equation

HRID 538098 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][NH2:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][C:14](C)(C)C([O-])([O-])[O-]>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][C:9]1[O:10][C:13]([CH3:14])=[N:12][N:11]=1

Participants

4

Reactant 2

HCID 21927715TrimethylorthoacetateHCID 58228857HCID 58228857, compound

Product 1

HCID 82481670HCID 82481670, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2-(3-bromophenyl)acetohydrazide 1104 (1.0 g, 4.37 mmol) in AcOH (10 mL) was added trimethylorthoacetate (2.62 g, 21.83 mmol) and the mixture heated to 115° C. for 18 hours. The volatiles were removed under reduced pressure and the residue purified by reverse phase chromatography to give 0.59 g of 2-(3-bromobenzyl)-5-methyl-1,3,4-oxadiazole 1105. 1H NMR 300 MHz CDCl3: δ 7.45 (m, 2H), 7.23 (m, 2H), 4.12 (s, 2H), 2.49 (s, 3H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue purified by reverse phase chromatography

Sources & evidence

ORD record
ord-ebd98dcea4ee4510836dbc2e618f03f0
Source dataset
uspto-grants-2014_10
Patent number
US08865718B2

Reaction notes

Loading…