Water → 5-(4-Cyanophenyl)-3-formyl-1,2,4-oxadiazole

HRID 54541Notes

Reaction equation

HRID 54541 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14][OH:15])[N:10]=2)=[CH:5][CH:4]=1)#[N:2].C1(N=C=NC2CCCCC2)CCCCC1.OP(O)(O)=O.O>CS(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([CH:14]=[O:15])[N:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 10868DicyclohexylcarbodiimideHCID 199591695-(4-Cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazole

Product 1

HCID 199593005-(4-Cyanophenyl)-3-formyl-1,2,4-oxadiazoleYield 53.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-(4-cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazole (4.08 g), N,N'-dicyclohexylcarbodiimide (20.92 g) and o-phosphoric acid (9.94 g) in dimethyl sulfoxide (80 ml) was stirred at ambient temperature. After 1 hour, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from ether to give 5-(4-cyanophenyl)-3-formyl-1,2,4-oxadiazole (2.17 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-78f49eade0944f58b25de858d4f6fe5b
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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