2-Chloro-1,1-diethoxyethane → Thiazole, 2-[(3,4,4-trifluoro-3-butenyl)thio]-

HRID 1793116Notes

Reaction equation

[C:1](=[S:11])([S:3][CH2:4][CH2:5][C:6]([F:10])=[C:7]([F:9])[F:8])[NH2:2].[CH2:12](OC(OCC)CCl)[CH3:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[F:10][C:6](=[C:7]([F:9])[F:8])[CH2:5][CH2:4][S:3][C:1]1[S:11][CH:12]=[CH:13][N:2]=1

Participants

Conditions

Temperature: 95 °C

Procedure

3 g (14.9 mmol) of 3,4,4-trifluoro-3-butenyl dithiocarbamate in 15 ml of glacial acetic acid are admixed with 2.3 g (15.1 mmol) of chloroacetaldehyde diethyl acetal and 40 mg of p-toluenesulphonic acid monohydrate. The mixture is stirred at 95° C. for 1.5 h and, after cooling to room temperature, is then concentrated by evaporation under reduced pressure. The evaporation residue is taken up in dichloromethane and washed with 1 N sodium hydroxide solution, and the organic phase is removed, dried over Na2SO4 and concentrated by evaporation under reduced pressure. 2.8 g (81.5% of theory; purity by GC/MS: 97.7 area %) of an oil are obtained.

Workup

temperatureafter cooling to room temperature
concentrationis then concentrated by evaporation under reduced pressure
washwashed with 1 N sodium hydroxide solution
customthe organic phase is removed
dry with materialdried over Na2SO4
concentrationconcentrated by evaporation under reduced pressure
custom2.8 g (81.5% of theory; purity by GC/MS: 97.7 area %) of an oil are obtained

Sources & evidence

ORD record: ord-ee4b179577564cf2a3db73ccda4e6fac
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078527B2

Reaction notes

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