Ethyl cyanoformate → Ethyl 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylate

HRID 453092Notes

Reaction equation

HRID 453092 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2OC(=O)[S:11][N:10]=2)=[CH:5][CH:4]=1.[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:16]>CCCCCCCCCCCC>[CH2:20]([O:19][C:17]([C:15]1[S:11][N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:16]=1)=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 8194565-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-one

Product 1

HCID 12601460Ethyl 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylateYield 40.5%

Reagents, catalysts & solvents 1

HCID 8182DodecaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one (0.47 g, 2.24 mmol) in n-dodecane (0.70 ml) was added ethyl cyanoformate (0.90 ml, 8.10 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 (3×50 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue washed with ether to get the desired product (0.24 g, 40%). MS ES+ (265.08).

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. washThe crude residue washed with ether

Sources & evidence

ORD record
ord-4bb2139793084281a350d1c201e06bc2
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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