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

HRID 1973092Notes

Reaction equation

HRID 1973092 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 powdered calcium chloride are saturated with hydrogen chloride gas at 15° C. within 2.5 hours and then stirred for an additional 3 hours. After the addition of 0.8 g. of active carbon, the precipitate is removed by filtration and washed with benzene. The benzene phase is evaporated under reduced pressure, and there is obtained 10-chloro-10,11-dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin having a melting point of 120°-123° C.

Workup

  1. additionAfter the addition of 0.8 g
  2. customof active carbon, the precipitate is removed by filtration
  3. washwashed with benzene
  4. customThe benzene phase is evaporated under reduced pressure

Sources & evidence

ORD record
ord-b7eaea481e3543b987b488cc751ca4f4
Source dataset
uspto-grants-1976_12
Patent number
US03996229

Reaction notes

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