Reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH:13]([SH:15])[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:16](=[S:18])=[S:17].Cl[CH2:20][C:21]#[N:22]>O1CCCC1>[C:16](=[S:18])([S:15][CH:13]([CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[S:17][CH2:20][C:21]#[N:22]Participants
Conditions
- Temperature
- 18 °C
Procedure
To a solution of 5.6 g (50 mmol) of potassium t-butoxide in 100 ml of tetrahydrofuran is added 8.7 ml (8.94 g, 60 mmol) of 92% 1-phenylethylmercaptan while maintaining the temperature of the reaction mixture between 20° and 25° C. The resulting suspension is cooled to 18° C. and 4.35 ml (72 mmol) of carbon disulfide is added thereto. The yellow solution which forms is stirred for 0.5 hours and then 3.23 ml (50 mmol) of chloroacetonitrile is added while the temperature of the reaction mixture is maintained at about 20° C. After stirring for 0.5 hour, the mixture is concentrated in vacuo. The residue is taken up in ether and the ether solution washed with water, brine, dried with Na2SO4 and concentrated in vacuo. The residue is chromatographed on a silica gel dry-column and eluted with 1:2 CH2Cl2 -hexane. The yellow band is collected to give 11.25 g (89%) of a yellow oil, cyanomethyl α-methylbenzyl trithiocarbonate.
Workup
- temperaturewhile maintaining the temperature of the reaction mixture between 20° and 25° C
- temperatureis maintained at about 20° C
- stirringAfter stirring for 0.5 hour
- concentrationthe mixture is concentrated in vacuo
- washthe ether solution washed with water, brine
- dry with materialdried with Na2SO4
- concentrationconcentrated in vacuo
- customThe residue is chromatographed on a silica gel dry-column
- washeluted with 1:2 CH2Cl2 -hexane
- customThe yellow band is collected
Sources & evidence
- ORD record
- ord-d0d0f116bb3947b7aefd57f2f81d3661
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04197311
Linked notes
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