Phosphorus oxide (P4O10) → 2-tert-Butyl-5-(3-methyl-4-nitrophenyl)-1,3,4-oxadiazole

HRID 2121836Notes

Reaction equation

HRID 2121836 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][C:16]([CH3:34])([CH3:33])[C:17]([NH:19][NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([CH3:31])[CH:23]=1)=O>C1(C)C=CC=CC=1>[CH3:15][C:16]([C:17]1[O:32][C:21]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([CH3:31])[CH:23]=2)=[N:20][N:19]=1)([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 23434365N'-(2,2-dimethylpropanoyl)-3-methyl-4-nitrobenzhydrazide

Product 1

HCID 224812152-tert-Butyl-5-(3-methyl-4-nitrophenyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus pentoxide (10 g) is added to a suspension of N′-(2,2-dimethylpropanoyl)-3-methyl-4-nitrobenzhydrazide (5.1 g) in toluene (200 ml). After refluxing for 2 h, the reaction mixture is poured into ice-water and extracted with diethyl ether. The organic phases are combined, dried over magnesium sulphate, evaporated and purified by chromatography on silica (eluent: 2/1 diethyl ether/petroleum ether) to give 2-(1,1-dimethylethyl)-5-(3-methyl-4-nitrophenyl)-1,3,4-oxadiazole.

Workup

  1. temperatureAfter refluxing for 2 h
  2. extractionextracted with diethyl ether
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. custompurified by chromatography on silica (eluent: 2/1 diethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-ea165b3c2aaf415db229312fd0a2aad7
Source dataset
uspto-grants-2004_02
Patent number
US06696487B2

Reaction notes

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