Chloroacetonitrile → p-Cyanothiobenzoic Acid S-Cyanomethyl Ester

HRID 1414018

Reaktionsgleichung

Reaktionsgleichung von HRID 1414018
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]

Komponenten

6

Edukt 3

HCID 7856ChloroacetonitrileHCID 801724-Cyanobenzoyl chlorideHCID 101753Sodium Trithiocarbonate

Produkt 1

HCID 12898768p-Cyanothiobenzoic Acid S-Cyanomethyl EsterAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4226208b34be40b7890bfdd0b21076fb
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04252814

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