Methyl chloroformate → HCID 44274303, compound

HRID 1283814Notes

Reaction equation

HRID 1283814 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]([O:28][CH3:29])=[O:27]>O1CCOCC1>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:10]=2)=[CH:3][C:2]=1[NH:1][C:26](=[O:27])[O:28][CH3:29]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 21390701HCID 21390701, compound

Product 1

HCID 44274303HCID 44274303, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 5-(3-amino-4-chlorophenyl)-3-(2-furanyl)-1,2,4-oxadiazole (1.35 g) and 1.05 g of potassium carbonate in 30 ml of dioxane, 0.75 g of methyl chloroformate is added. The resulting mixture is heated at reflux for 16 hours, concentrated to dryness and the residue placed on an alumina column. The product is eluted with benzene to yield 0.45 g of the title compound, melting point 200°-201°C.

Workup

  1. additionis added
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for 16 hours
  4. concentrationconcentrated to dryness
  5. washThe product is eluted with benzene

Sources & evidence

ORD record
ord-3b88d2f10a864edcae364560553762af
Source dataset
uspto-grants-1976_08
Patent number
US03976657

Reaction notes

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