Ethyl cyanoformate → HCID 16756983, compound

HRID 453093Notes

Reaction equation

HRID 453093 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2OC(=O)[S:12][N:11]=2)=[CH:6][CH:5]=1.[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:19]>CCCCCCCCCCCC>[CH2:23]([O:22][C:20]([C:18]1[S:12][N:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:16])([F:1])[F:17])=[CH:9][CH:8]=2)[N:19]=1)=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 59549536HCID 59549536, compound

Product 1

HCID 16756983HCID 16756983, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 8182DodecaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-(4-trifluoromethoxyphenyl)-[1,3,4]oxathiazol-2-one (0.74 g, 2.81 mmol) in n-dodecane (0.50 ml) was added ethyl cyanoformate (1.10 ml, 11.24 mmol). The resulting reaction mixture was refluxed for 24 h at 150° C. After the completion of the reaction (TLC monitoring), added ice-cold water and extracted with ethyl acetate (3×50 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, 2% EtOAc-Hexane) to get the product (0.11 g, 12%).

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 (3×50 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, 2% EtOAc-Hexane)

Sources & evidence

ORD record
ord-65c244fb7f7544079333ced3f7e27ed6
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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