Benzyl mercaptan → HCID 11076271, compound
Reaction equation
CC(C)([O-])C.[K+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:16]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19]>CN(C)C=O>[Cl:24][C:23]1[C:16]([S:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a suspension of 112.1 g of potassium-t-butoxide in 1000 mL of dimethylformamide under a nitrogen atmosphere, 124.3 g of benzylmercaptan was added dropwise while maintaining the reaction temperature at 20°-25° C. with an ice-water bath. After stirring at 25° C. for 1.5 hours, a solution of 175 g of 2,3-dichlorobenzaldehyde dissolved in 750 mL of N,N-dimethylformamide was added dropwise, while maintaining the reaction temperature at 25°-40° with a water bath. After stirring at 25° C. for 12 hours, the reaction mixture was poured onto excess ice water to yield a precipitate. The suspension was filtered, and the isolated solid was washed with water, suction-dried and finally dried in vacuo at 40° C. overnight to afford 201 g of the title compound as a light yellow solid; m.p. 65°-68° C.
Workup
- temperaturewhile maintaining the reaction temperature at 20°-25° C. with an ice-water bath
- additionwas added dropwise
- temperaturewhile maintaining the reaction temperature at 25°-40° with a water bath
- stirringAfter stirring at 25° C. for 12 hours
- customto yield a precipitate
- filtrationThe suspension was filtered
- washthe isolated solid was washed with water
- customsuction-dried
- customfinally dried in vacuo at 40° C. overnight
Sources & evidence
- ORD record
- ord-82552ca2f2064709ae1345a6b09bfb87
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04981506
Reaction notes
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