Hydrochloric Acid → 1-Chloro-3-(chloromethyl)-2-[(phenylmethyl)thio]benzene

HRID 703040Notes

Reaction equation

[Cl:1][C:2]1[C:3]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH2:8]O)[CH:5]=[CH:6][CH:7]=1.CN(C)C1C=CC=CC=1.S(Cl)([Cl:29])=O.Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Cl:29])[C:3]=1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 15 °C

Procedure

To a mixture of 54 g of the compound of Example 2 in 200 mL of chloroform (ethanol-free) and of N,N-dimethylaniline, a solution of 30 g of thionyl chloride in 50 mL of chloroform (ethanol-free) was added while maintaining the reaction temperature at 15° C. with an ice-water bath. The mixture was stirred at 25° C. for 1 hour, then refluxed for 3 hours. The mixture was acidified with 1 N aqueous hydrochloric acid and the organic layer was collected. The organic layer was washed once with 1 N aqueous hydrochloric acid, dried over magnesium sulfate, and filtered. The filtrate was passed through a silica gel column, eluted with methylene chloride, and after evaporation of the eluant, 54 g subject compound was obtained as a yellow oil.

Workup

temperaturerefluxed for 3 hours
customthe organic layer was collected
washThe organic layer was washed once with 1 N aqueous hydrochloric acid
dry with materialdried over magnesium sulfate
filtrationfiltered
washeluted with methylene chloride
customafter evaporation of the eluant, 54 g
customwas obtained as a yellow oil

Sources & evidence

ORD record: ord-5dca56f7926e4788b9ab83c874d4524c
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04981506

Reaction notes

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