Ethyl cyanoformate → HCID 12351253, compound

HRID 453091Notes

Reaction equation

HRID 453091 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2OC(=O)[S:10][N:9]=2)=[CH:4][CH:3]=1.[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:15]>CCCCCCCCCCCC>[CH2:19]([O:18][C:16]([C:14]1[S:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:15]=1)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 8194535-(4-chlorophenyl)-1,3,4-oxathiazol-2-one

Product 1

HCID 12351253HCID 12351253, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 8182DodecaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-(4-chlorophenyl)-[1,3,4]oxathiazol-2-one (0.60 g, 2.80 mmol) in n-dodecane (0.80 ml) was added ethyl cyanoformate (1.10 ml, 11.20 mmol). The resulting reaction mixture was refluxed for 20 h at 150° C. After the completion of the reaction (TLC monitoring), added ice-cold water and extracted with ethyl acetate (3×75 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 20% EtOAc—Hexane) to get the product (0.23 g, 30%).

Workup

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. additionadded ice-cold water
  4. extractionextracted with ethyl acetate (3×75 ml)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude residue was purified over silica gel (100-200 M, 20% EtOAc—Hexane)

Sources & evidence

ORD record
ord-48a97d4577da42ad82688d254239c45b
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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