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Hydrochloric Acid → 2-Chloro-11-[beta-(methylamino)ethylthio]dibenzo[b,f]thiepin hydrochloride

HRID 867466
Notes
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Reaction equation

HRID 867466 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]=[C:10]([S:11][CH2:12][CH2:13][N:14](C)[C:15](OC3C=CC=CC=3)=O)[C:4]=2[CH:3]=1.[OH-].[K+].Cl>C(O)CO>[ClH:1].[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]=[C:10]([S:11][CH2:12][CH2:13][NH:14][CH3:15])[C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 155683262-chloro-11-[beta-(N-methyl-N-phenoxycarbonylamino)ethylthio]dibenzo[b,f]thiepin

Product 1

HCID 127949572-Chloro-11-[beta-(methylamino)ethylthio]dibenzo[b,f]thiepin hydrochloride

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 5.6 g of 2-chloro-11-[β-(N-methyl-N-phenoxycarbonylamino)ethylthio]dibenzo[b,f]thiepin, Example 6, 127 ml of ethylene glycol and 10.8 g of potassium hydroxide is stirred at 150°-155° C. for 30 minutes. Thereafter the reaction mixture is poured onto 300 ml of ice-water and the aqueous mixture is extracted with an ether-toluene (1:1) mixture. The combined extracts, successively, are washed well with water, dried and filtered and the filtrate evaporated leaving an orange oil. The oil is converted to its hydrogen chloride acid salt which is recrystallized from a methanol-acetone-ether mixture to give the product, mp 194°-196° C. of 2-chloro-11-[β-(methylamino)ethylthio]dibenzo[b,f]thiepin hydrochloride.

Workup

  1. extractionthe aqueous mixture is extracted with an ether-toluene (1:1) mixture
  2. washThe combined extracts, successively, are washed well with water
  3. customdried
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customleaving an orange oil
  7. customis recrystallized from a methanol-acetone-ether mixture

Sources & evidence

ORD record
ord-e1b425fcbac44df6a55d43bfd0f0d48a
Source dataset
uspto-grants-1988_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04775682

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes