Hydrochloric Acid → (4-Ethoxymethylsulfanyl-phenyl)-acetic acid ethyl ester

HRID 505583Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)[CH3:2].N1C=CC=CC=1.Cl[CH2:21][O:22][CH2:23][CH3:24].Cl>C(#N)C.O>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:21][O:22][CH2:23][CH3:24])=[CH:8][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A 100 mL 3-necked round bottom flask is charged with (4-mercapto-phenyl)-acetic acid ethyl ester (10 g, 0.0151 mol), followed by the addition of (20 mL) acetonitrile. The reaction mixture is cooled to 0° C. followed by the addition of 10 mL (0.13 mol) of pyridine and 5.30 g (0.056 mol) of chloromethylethyl ether in 10 mL of acetonitrile in a dropwise manner. The reaction mixture is brought to RT followed by heating at reflux for 24 h. The reaction is worked up by evaporating the solvent under vacuum. The residue thus obtained is diluted with water (20 mL) followed by addition of di lute aqueous hydrochloride solution. This is extracted with ethyl acetate (2×100 mL). The organic layer is washed with dilute aqueous hydrochloric acid solution, water and finally with brine. The organic layer is dried over sodium sulfate and evaporated under vacuum to give (4-ethoxymethylsulfanyl-phenyl)-acetic acid ethyl ester as yellow oil.

Workup

customis brought to RT
temperatureby heating
temperatureat reflux for 24 h
customby evaporating the solvent under vacuum
customThe residue thus obtained
extractionThis is extracted with ethyl acetate (2×100 mL)
washThe organic layer is washed with dilute aqueous hydrochloric acid solution, water and finally with brine
dry with materialThe organic layer is dried over sodium sulfate
customevaporated under vacuum

Sources & evidence

ORD record: ord-22a71a45bb494ec58e2e785735004c81
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781451B2

Reaction notes

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