Thionyl Chloride → HCID 20310099, compound

HRID 1606734Notes

Reaction equation

HRID 1606734 reaction equation
[C:1]([CH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([OH:14])=O)[C:6]=2[CH2:5][CH2:4]1)#[N:2].S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[C:1]([CH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([Cl:17])=[O:14])[C:6]=2[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12944295HCID 12944295, compound

Product 1

HCID 20310099HCID 20310099, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 6.0 g. of 1-cyanoindan-4-carboxylic acid are added 20 ml. of chloroform and 80 ml. of thionyl chloride and the mixture is allowed to stand at room temperature for 15 hours. The excess thionyl chloride and chloroform are distilled off under reduced pressure. To 1-cyanoindan-4-carbonyl chloride, which is thus obtained as the distillation residue, is added 100 ml. of chlorobenzene, followed by stirring under cooling with ice. Then, 6.0 g. of anhydrous aluminum chloride powder is added and the temperature is gradually increased to about 80°C, at which temperature the reaction mixture is stirred for 2.5 hours. After cooling, ice-hydrochloric acid is added, followed by extraction with ether. The extract is washed with water and dried. Then, the solvent is distilled off under reduced pressure and the residue obtained is purified by column chromatography on silica gel (700 g. silica gel; eluant: chloroform). The described procedure gives 4-(p-chlorobenzoyl)indan-1-carbonitrile as an oily product.

Workup

  1. distillationThe excess thionyl chloride and chloroform are distilled off under reduced pressure

Sources & evidence

ORD record
ord-68ce2d839554492da1de7dcab7a4c4a3
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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