氯乙腈 → p-Cyanothiobenzoic Acid S-Cyanomethyl Ester

HRID 1414018

反应方程式

HRID 1414018 反应方程式
Cl[CH2:2][C:3]#[N:4].C(=S)([S-])[S-:6].[Na+].[Na+].[C:11]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)#[N:12]>ClCCl.CCCCCC>[C:3]([CH2:2][S:6][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([C:11]#[N:12])=[CH:14][CH:15]=1)#[N:4]

参与物

6

反应物 3

HCID 7856氯乙腈HCID 80172对氰基苯甲酰氯HCID 101753三硫代碳酸钠

产物 1

HCID 12898768p-Cyanothiobenzoic Acid S-Cyanomethyl Ester收率 103.7%

试剂、催化剂与溶剂 2

HCID 6344二氯甲烷溶剂HCID 8058正己烷溶剂

反应条件

温度
5 °C

实验过程

Chloroacetonitrile (13.1 ml; 0.203 mol) is added over 15 minutes to a cold (15° C.) 2 N solution of sodium trithiocarbonate (92.5 ml; 0.185 mol). The reaction mixture is stirred one hour at 5° C., extracted with ether, and the aqueous layer added dropwise to a solution of p-cyanobenzoyl chloride (20.9 g; 0.124 mol) in dichloromethane (40 ml). During addition, the temperature of the reaction mixture is held below 12° C. The reaction mixture is then held at 0°-5° C. for 2 hours, diluted with hexane (50 ml) and filtered to yield 26 g of a yellow solid. This solid is recrystallized from a mixture of acetone-methanol-water to afford 19.7 g of title product, a yellowish solid, melting point 129°-131° C.

后处理

  1. extractionextracted with ether
  2. additionDuring addition
  3. customis held below 12° C
  4. waitThe reaction mixture is then held at 0°-5° C. for 2 hours
  5. filtrationfiltered

来源与证据

ORD记录
ord-4226208b34be40b7890bfdd0b21076fb
来源数据集
uspto-grants-1981_02
专利号
US04252814

关联笔记

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