Hydrochloric Acid → 2-Hydroxy-9-ethoxycarbonyl-10,11-dihydrodibenzo[b,f]thiepin

HRID 261550Notes

Reaction equation

HRID 261550 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][C:7]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl.[CH2:21](O)[CH3:22]>C(OCC)(=O)C.C1C=CC=CC=1>[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][C:7]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([O:17][CH2:21][CH3:22])=[O:16])[C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 233370412-Hydroxy-9-carboxy-10,11-dihydrodibenzo[b,f]thiepin

Product 1

HCID 126871252-Hydroxy-9-ethoxycarbonyl-10,11-dihydrodibenzo[b,f]thiepinYield 85%

Reagents, catalysts & solvents 1

HCID 21583983Benzene ethyl acetateSolvent

Procedure

An amount of 1.7 g of 2-hydroxy-9-carboxy-10,11-dihydrodibenzo[ b,f] thiepin was dissolved in 50 ml of anhydrous ethanol and the mixture was refluxed for 3 hours, while hydrogen chloride gas was bubbled into the mixture. The solvent was distilled off to obtain the residue which was dissolved in the mixed solvent of ethyl acetate-benzene. The solution was washed with saturated sodium chloride solution and freed of solvent by distillation to obtain 1.6 g (85%) of 2-hydroxy-9-ethoxycarbonyl-10,11-dihydrodibenzo[b,f]thiepin as brown crystals having a melting point of 125°-129° C.

Workup

  1. customwas bubbled into the mixture
  2. distillationThe solvent was distilled off
  3. customto obtain the residue which
  4. washThe solution was washed with saturated sodium chloride solution
  5. distillationfreed of solvent by distillation

Sources & evidence

ORD record
ord-c5c03ba49e764c6689d82ebf3ba22f88
Source dataset
uspto-grants-1979_08
Patent number
US04166127

Reaction notes

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