Sodium Bicarbonate → 2-Tert-butyl-5-(chloromethyl)-1,3,4-oxadiazole

HRID 2261309

Reaction equation

HRID 2261309 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=O.C(=O)(O)[O-].[Na+]>O>[C:8]([C:7]1[O:12][C:3]([CH2:2][Cl:1])=[N:5][N:6]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 54595759N'-(2-chloroacetyl)-2,2-dimethylpropanehydrazide

Product 1

HCID 167787622-Tert-butyl-5-(chloromethyl)-1,3,4-oxadiazoleYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.34 g of N′-(chloroacetyl)-2,2-dimethylpropanohydrazide and 6.6 g of polyphosphoric acid was stirred at 90° C. for 10 hours. The reaction mixture was cooled to room temperature. After 200 ml of water and then sodium bicarbonate were added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1.12 g of 2-t-butyl-5-(chloromethyl)-1,3,4-oxadiazole.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb856fa08426417186d5bd3dcc06cc15
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Linked notes

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