Dimethylformamide → 3-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]benzonitrile

HRID 732126Notes

Reaction equation

HRID 732126 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]1[O:16][C:7]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[C:14]#[N:15])=[N:6][N:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14812Phosphorus oxide (P4O10)HCID 54595588N'-(2-chloroacetyl)-3-cyanobenzohydrazide

Product 1

HCID 201189383-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]benzonitrileYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N′-(chloroacetyl)-3-cyanobenzohydrazide (795 mg, 3.34 mmol) and P2O5 (4.7 g, 33.4 mmol) were added to DMF (6 ml) and toluene (4 ml). The reaction mixture was refluxed for 2 h. K2CO3 (aq., sat.) was added until pH was basic and the mixture was extracted with DCM. The combined organic layers were dried (Na2SO4) and purified with flash chromatography using 0 to 100% EA in hep. to give the title compound (209 mg, 29%). 1H NMR: 8.29 (m, 2 H), 7.82 (m, 1 H), 7.66 (t, 1 H), 4.78 (s, 2 H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionthe mixture was extracted with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. custompurified with flash chromatography

Sources & evidence

ORD record
ord-33fd2f48fe344da6b7e6d9886e41e977
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

Loading…