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

HRID 453112Notes

Reaction equation

HRID 453112 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2OC(=O)[S:10][N:9]=2)=[C:4]([O:14][CH3:15])[CH:3]=1.[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:17]>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:10][N:9]=2)=[C:4]([O:14][CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 595495245-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-one

Product 1

HCID 59549519Ethyl 3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazole-5-carboxylateYield 19.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-(4-chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-one (1.32 g, 5.42 mmol) in 1,2-dichlorobenzene (5 ml) was added ethyl cyanoformate (2.20 ml, 21.67 mmol). The resulting reaction mixture was refluxed for 24 h at 150° C. After the completion of the reaction (TLC monitoring), the reaction mass was as such (direct loading) purified through flash chromatography (100-200 M silica, 5% EtOAc-Hexane) to get the desired product (0.31 g, 19%). LCMS: 299.29 (M+H)+, 98.99%.

Workup

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. custompurified through flash chromatography (100-200 M silica, 5% EtOAc-Hexane)

Sources & evidence

ORD record
ord-1c2a13eb95064be5934050f17c8e6581
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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