Phosphorus oxychloride → 5-(4-isopropylphenyl)-1,3,4-oxadiazol-2(3H)-one

HRID 2172165Notes

Reaction equation

HRID 2172165 reaction equation
C(OC(=O)[CH2:5][NH:6][NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=1)C.P(Cl)(Cl)(Cl)=[O:21]>>[CH:15]([C:12]1[CH:13]=[CH:14][C:9]([C:8]2[O:18][C:5](=[O:21])[NH:6][N:7]=2)=[CH:10][CH:11]=1)([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 90697033Ethyl[2-(4-isopropylbenzoyl)hydrazino]acetate

Product 1

HCID 3129205-(4-isopropylphenyl)-1,3,4-oxadiazol-2(3H)-oneYield 58%

Procedure

Ethyl[2-(4-isopropylbenzoyl)hydrazino]acetate (4.85 g, 19.4 mmol) is treated with phosphorus oxychloride (50 mL), heated to reflux for 3 h, and then poured onto ice. The precipitate is collected and washed thoroughly with water and dried in the air to furnish 5-(4-isopropylphenyl)-1,3,4-oxadiazol-2(3H)-one (2.30 g, 58%) MS (ES+): m/e 205.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. additionpoured onto ice
  4. customThe precipitate is collected
  5. washwashed thoroughly with water
  6. customdried in the air

Sources & evidence

ORD record
ord-341e8dc483d74410aaed1e31c80f17a7
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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