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

HRID 1084979
Notes
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Reaction equation

HRID 1084979 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-021fca90dd1c410883817de4a7319a65
Source dataset
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05006664

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes