Thionyl Chloride → 5-chloro-3-methylthio-5H-dibenzo[a,d]cycloheptene

HRID 2290288Notes

Reaction equation

HRID 2290288 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][S:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:16]=[CH:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH:12](O)[C:11]=2[CH:22]=1>C1C=CC=CC=1>[Cl:3][CH:12]1[C:11]2[CH:22]=[C:7]([S:6][CH3:5])[CH:8]=[CH:9][C:10]=2[CH:16]=[CH:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]1=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 202322443-methylthio-5H-dibenzo[a,d]cyclohepten-5-ol

Product 1

HCID 202322695-chloro-3-methylthio-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Molar excess (5 milliliters) of thionyl chloride was added to a solution of the 3-methylthio-5H-dibenzo[a,d]cyclohepten-5-ol intermediate in 45 milliliters of benzene and the resulting mixture heated under reflux for two hours to obtain a 5-chloro-3-methylthio-5H-dibenzo[a,d]cycloheptene (chloro compound) intermediate in the reaction mixture. The reaction mixture was subjected to reduced pressure to co-evaporate benzene and unreacted thionyl chloride, and the procedure repeated with several additions of benzene to obtain a purified chloro compound intermediate.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for two hours

Sources & evidence

ORD record
ord-72d4825da18f4bbb83c4bd7b1fc15662
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

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