Ethyl cyanoformate → Ethyl 3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazole-5-carboxylate

HRID 453119Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1OC(=O)[S:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])#[N:23]>ClC1C=CC=CC=1Cl>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[S:18][N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-(2-(benzyloxy)-4-chlorophenyl)-1,3,4-oxathiazol-2-one (0.15 g, 0.47 mmol) in 1,2-dichlorobenzene (1 ml) was added ethyl cyanoformate (185 μL, 1.88 mmol). The resulting reaction mixture was refluxed for 3 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, 2% EtOAc-Hexane) to get the desired product (0.02 g, 12%). MS: 375.18 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-8ced0ef0bb884568a1eb20f12a8a9aa3
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492414B2

Reaction notes

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