Hydrochloric Acid → HCID 20316447, compound

HRID 2418981Notes

Reaction equation

HRID 2418981 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([OH:19])=[O:18].Cl.[CH3:21]O>>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([O:19][CH3:21])=[O:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12443712HCID 12443712, compound

Product 1

HCID 20316447HCID 20316447, compound

Procedure

A solution of 950 mg. of 10,11-dihydrodibenzo[b.f]thiepin-2-acetic acid in 50 ml. of methanol is saturated with hydrogen chloride. After 2 hours the reaction mixture is evaporated under reduced pressure and the residue is chromatographed on silica gel using ethyl acetate:hexane (1:7) as eluant to yield methyl 10,11-dihydrodibenzo[b.f]-thiepin-2-acetate (XII, R1 = Me), which is dissolved in 10 ml. of benzene and treated with 900 mg. of 85% m-chloroperbenzoic acid dissolved in 10 ml. of dimethoxyethane. After 5 minutes, 3 ml. of saturated aqueous sodium sulfite is added, followed by 1 ml. of saturated aqueous potassium carbonate. The organic layer is separated, dried with anhydrous magnesium sulfate and filtered through a column of 20 g. of silica gel, eluting with benzene. Evaporation of the eluate under reduced pressure yields a residue which upon recrystallization from chloroform:hexane (1:1) yields 900 mg. of methyl 10,11-dihydrodibenzo[b.f]thiepin-2-acetate-S,S-dioxide (XV, R1 = Me), having a melting point of 103°-105° C.

Workup

  1. customAfter 2 hours the reaction mixture is evaporated under reduced pressure
  2. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-40fb49cf0e374c73af57380c164680ed
Source dataset
uspto-grants-1978_08
Patent number
US04104280

Reaction notes

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