Ethyl chloroformate → HCID 135444596, compound

HRID 1196616Notes

Reaction equation

HRID 1196616 reaction equation
[Cl:1][C:2]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]([Cl:20])[C:3]=1[NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7](=[N:9][OH:10])[NH2:8].Cl[C:22](OCC)=[O:23]>N1C=CC=CC=1>[Cl:1][C:2]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]([Cl:20])[C:3]=1[NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]1[NH:8][C:22](=[O:23])[O:10][N:9]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 86745844HCID 86745844, compound

Product 1

HCID 135444596HCID 135444596, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a room temperature solution of 2-(2,6-dichloro-3-methylanilino)benzamide oxime (585 mg, 1.89 mmols) in 5 mL of pyridine is added ethyl chloroformate (250 μL, 2.62 mmols). The solution is heated at reflux for 1 hour, cooled, and concentrated in vacuo. Flash chromatography eluting with 2:1 hexane: ethyl acetate provides 295 mg (47%) of 3-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-1,2,4-oxadiazol-5(4H)-one as a white solid;

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. washFlash chromatography eluting with 2:1 hexane

Sources & evidence

ORD record
ord-05104106050142ce826063019972169a
Source dataset
uspto-grants-1992_05
Patent number
US05114958

Reaction notes

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