Ethyl cyanoformate → Ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate

HRID 1080610Notes

Reaction equation

HRID 1080610 reaction equation
[C:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])#[N:2].[CH:8]([C:11]1OC(=O)[S:13][N:12]=1)([CH3:10])[CH3:9]>CC1C=CC(C)=CC=1>[CH:8]([C:11]1[N:2]=[C:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:13][N:12]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 15389973HCID 15389973, compound

Product 1

HCID 15389974Ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

Ethyl cyanoformate (38.6 g, 0.39 mol) is added to a stirred solution of 5-isopropyl-[1,3,4]oxathiazolin-2-one (18.5 g, 0.13 mol) in p-xylene (180 ml). The mixture is refluxed for 6 hours and then the solvent is evaporated in vacuo to give crude ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate (25.2 g, 97%) as a yellow oil, which is used without purification for the next step.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-bcbc5426c3784772a3d93cad21d9dbe5
Source dataset
uspto-grants-1996_12
Patent number
US05583092

Reaction notes

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