Hydrochloric Acid → 10-Chloro-10,11-dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin

HRID 1075874Notes

Reaction equation

HRID 1075874 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11](O)[C:10]3[CH:14]=[C:15]([S:18][CH3:19])[CH:16]=[CH:17][C:9]=3[S:8][C:7]=2[CH:20]=1.[Cl-:21].[Ca+2].[Cl-].Cl>C1C=CC=CC=1>[Cl:21][CH:11]1[C:10]2[CH:14]=[C:15]([S:18][CH3:19])[CH:16]=[CH:17][C:9]=2[S:8][C:7]2[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5284359Calcium ChlorideHCID 1282219810,11-Dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-ol

Product 1

HCID 1282220110-Chloro-10,11-dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

15.7 G. of 10,11-dihydro-3-methoxy-8-(methylthio)-dibenzo[b,f]thiepin-10-ol, 250 ml. of benzene and 6 g. of finely pulverized calcium chloride are saturated with hydrochloric acid gas over a period of 21/2 hours at 15° and subsequently stirred for an additional 3 hours. After the addition of 0.8 g. of activated charcoal, the mixture is filtered and washed with benzene. The benzene phase is evaporated under reduced pressure, whereby there is obtained 10-chloro-10,11-dihydro-3-methoxy-8-(methylthio)-dibenzo[b,f]thiepin, having a melting point of 120°-123°.

Workup

  1. additionAfter the addition of 0.8 g
  2. filtrationof activated charcoal, the mixture is filtered
  3. washwashed with benzene
  4. customThe benzene phase is evaporated under reduced pressure

Sources & evidence

ORD record
ord-1a9ad2babc0e49489da96d7f991fb99e
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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