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

HRID 1075824Notes

Reaction equation

HRID 1075824 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[C:7]3[CH2:15][CH:14](O)[CH:13]=[C:12]([S:17][CH3:18])[C:8]=3[CH:9]=[CH:10][S:11][C:5]=2[CH:4]=1.[Cl-:21].[Ca+2].[Cl-].Cl>C1C=CC=CC=1>[Cl:21][CH:15]1[C:14]2[CH:13]=[C:12]([S:17][CH3:18])[CH:8]=[CH:9][C:10]=2[S:11][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][C:6]=2[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5284359Calcium ChlorideHCID 2154119710,11-Dihydro-3-methoxy-8-(methylthio)-dibenzo 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 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-2e458c8198a34ceebc77d0e0015b35a2
Source dataset
uspto-grants-1976_05
Patent number
US03954769

Reaction notes

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