Thionyl Chloride → (1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioate

HRID 1462908Notes

Reaction equation

HRID 1462908 reaction equation
[C:1]([S:9][CH2:10][CH:11]([CH3:15])[C:12](O)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>C1(C)C=CC=CC=1>[C:1]([S:9][CH2:10][CH:11]([CH3:15])[C:12]([Cl:18])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5694973-(Benzoylthio)-2-methylpropanoic acid

Product 1

HCID 12878433(1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Benzoylthio-2-methylpropanoic acid (11.6 g) in toluene (78 ml) was treated with thionyl chloride (4.6 ml). The resulting solution was warmed to 80° for 2.5 hours and then evaporated to dryness under reduced pressure to yield 3-benzoylthio-2-methylpropanoyl chloride. A solution of (±)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid hydrochloride (10.7 g) in pyridine (65 ml) was treated dropwise with the crude 3-benzoylthio-2-methylpropanoyl chloride with vigorous stirring. After stirring overnight, the reaction mixture was added to ice (900 g), acidified with 20% hydrochloric acid (130 ml), and extracted with ether (700 ml). The ether layer was dried over sodium sulfate and activated charcoal, and then concentrated to dryness to yield a viscous oil (25 g) which was dissolved in acetonitrile (100 ml) and treated with dicyclohexylamine (13 ml). The crystalline product, (±) 1-(3-benzoyl-2-methyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid dicyclohexylamine salt, was collected by filtration; yield 3.6 g, m.p. 170°-173°.

Workup

  1. temperatureThe resulting solution was warmed to 80° for 2.5 hours
  2. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ac8dadfaa875411492620e2c54c85f3c
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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