Sodium Chloride → 4-(5,6,7,8-Tetrahydroquinoline-8-ylthio)-benzonitrile

HRID 231541

Reaction equation

HRID 231541 reaction equation
Cl.Cl[CH:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.[SH:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C)C=O>[N:11]1[C:12]2[CH:3]([S:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH2:4][CH2:5][CH2:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 5850584-ThiobenzonitrileHCID 137121818-Chloro-5,6,7,8-tetrahydroquinoline hydrochloride

Product 1

HCID 142812494-(5,6,7,8-Tetrahydroquinoline-8-ylthio)-benzonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.08 g (20 mmol) of 8-chloro-5,6,7,8-tetrahydroquinoline hydrochloride, 3.38 g (25 mmol) of 4-mercaptobenzonitrile and 6.91 g (50 mmol) of potassium carbonate in 34 ml of dimethylformamide was stirred under nitrogen at room temperature overnight. The mixture was poured into aqueous saturated sodium chloride and was extracted with ethyl acetate. The extract was washed with ice-cold aqueous 2N sodium hydroxide and water, dried over MgSO4 and evaporated under reduced pressure to obtain 4.72 g (89%) of 4-(5,6,7,8-tetrahydroquinoline-8-ylthio)-benzonitrile as colorless crystals (from methanoldichloromethane).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with ice-cold aqueous 2N sodium hydroxide and water
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b9bf01850e74443aa7151a3d49129b30
Source dataset
uspto-grants-1989_07
Patent number
US04847268

Linked notes

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