Methyl chloroformate → [4-(5-Phenyl-1,2,4-oxadiazol-3-yl)phenyl]carbamic acid, methyl ester

HRID 1415131Notes

Reaction equation

HRID 1415131 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[C:6]1([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:6]1([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:2](=[O:3])[O:4][CH3:5])=[CH:21][CH:22]=3)[N:13]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 5245795HCID 5245795, compound

Product 1

HCID 86734404[4-(5-Phenyl-1,2,4-oxadiazol-3-yl)phenyl]carbamic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.4 g. (0.015 mole) of methyl chloroformate is added to a mixture of 2.4 g. (0.01 mole) of 5-phenyl-3-(4-aminophenyl)-1,2,4-oxadiazole, from part (b), and 2.1 g. of potassium carbonate in 50 cc. of dioxane. The resulting mixture is refluxed for 0.5 hours. It is then concentrated to dryness and the residue is crystallized from benzene to yield [4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl]carbamic acid, methyl ester.

Workup

  1. temperatureThe resulting mixture is refluxed for 0.5 hours
  2. concentrationIt is then concentrated to dryness
  3. customthe residue is crystallized from benzene

Sources & evidence

ORD record
ord-ed434ab2a7a24910b3d3c78cbe7e1ee2
Source dataset
uspto-grants-1977_01
Patent number
US04003909

Reaction notes

Loading…