Carbon Disulfide → Cyanomethyl alpha-Methylbenzyl Trithiocarbonate

HRID 2049342

反応式

HRID 2049342 の反応式
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]

参加物

6

反応物 4

HCID 6348Carbon DisulfideHCID 7856ChloroacetonitrileHCID 1418501-PhenylethanethiolHCID 23665647Potassium tert-butoxide

生成物 1

HCID 20345060Cyanomethyl alpha-Methylbenzyl Trithiocarbonate収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
18 °C

実験手順

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.

後処理

  1. temperaturewhile maintaining the temperature of the reaction mixture between 20° and 25° C
  2. temperatureis maintained at about 20° C
  3. stirringAfter stirring for 0.5 hour
  4. concentrationthe mixture is concentrated in vacuo
  5. washthe ether solution washed with water, brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on a silica gel dry-column
  9. washeluted with 1:2 CH2Cl2 -hexane
  10. customThe yellow band is collected

出典と根拠

ORDレコード
ord-d0d0f116bb3947b7aefd57f2f81d3661
出典データセット
uspto-grants-1980_04
特許番号
US04197311

関連ノート

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