Methanesulfonyl chloride → HCID 15598427, compound

HRID 247403Notes

Reaction equation

[CH:1]1[C:11]2[C:10]([CH2:12][CH2:13][OH:14])=[C:9]([CH2:15][CH2:16][OH:17])[C:8]3[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:22][S:23]([O:14][CH2:13][CH2:12][C:10]1[C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[C:9]=1[CH2:15][CH2:16][O:17][S:23]([CH3:22])(=[O:25])=[O:24])(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

15 g (0.05 mole) of dibenzo[b,f]thiepine-10,11-diethanol are dissolved at room temperature in 60 ml of pyridine and the solution is treated dropwise in an ice-sodium chloride bath, at a reaction temperature of -5° C., with 8.4 ml (12.6 g, 0.11 mole) of methanesulphonyl chloride. The reaction mixture is subsequently stirred for 30 minutes at 0° C. and then for 1 hour at 15°-25° C. Together with 500 ml of methylene chloride the reaction mixture is then extracted in a separating funnel in succession with 400 ml of 2N hydrochloric acid and 400 ml of water. The methylene chloride solution is separated, dried over magnesium sulphate, and concentrated in a water jet vacuum to give as residue 10,11-bis-[2-(methylsulphonyloxy)-ethyl]-dibenzo[b,f]thiepine with a melting point of 107°-108° C.

Workup

waitfor 1 hour at 15°-25° C
extractionTogether with 500 ml of methylene chloride the reaction mixture is then extracted in a separating funnel in succession with 400 ml of 2N hydrochloric acid and 400 ml of water
customThe methylene chloride solution is separated
dry with materialdried over magnesium sulphate
concentrationconcentrated in a water jet vacuum

Sources & evidence

ORD record: ord-ffcb50b650e6462787207a527374bd39
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04707476

Reaction notes

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