Ethyl 4-cyanobenzoate → Ethyl 5-(4-ethoxycarbonylphenyl)-1,2,4-thiadiazole-3-carboxylate

HRID 1764058Notes

Reaction equation

HRID 1764058 reaction equation
O=C1[S:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])O1.[C:12]([C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1)#[N:13]>CC(C)=O>[CH2:21]([O:20][C:18]([C:17]1[CH:23]=[CH:24][C:14]([C:12]2[S:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:13]=2)=[CH:15][CH:16]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 81589Ethyl 4-cyanobenzoateHCID 12351252ethyl 2-oxo-2H-1,3,4-oxathiazole-5-carboxylate

Product 1

HCID 12351256Ethyl 5-(4-ethoxycarbonylphenyl)-1,2,4-thiadiazole-3-carboxylateYield 23.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.75 g (0.010 mol) of ethyl 2-oxo-1,3,4-oxathiazole-5-carboxylate and 17.5 g (0.10 mol) of ethyl p-cyanobenzoate was stirred at 190° C for 72 hours, cooled, and dissolved in acetone. Gc analysis of the solution revealed that the product had formed in 53% yield. Concentration of the solution to 90° C (0.1 torr) and two crystallizations of the residue from ethanol (charcoal) at -20° C gave 0.72 g (23.5%) of beige solid, mp 66°-67.5° C.

Workup

  1. temperaturecooled
  2. customhad formed in 53% yield
  3. customConcentration of the solution to 90° C (0.1 torr) and two crystallizations of the residue from ethanol (charcoal) at -20° C

Sources & evidence

ORD record
ord-786813501d9645aa9ca1ad2b40273be1
Source dataset
uspto-grants-1978_09
Patent number
US04115095

Reaction notes

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