Hydrochloric Acid → 2-Chloro-11-[beta-(methylamino)ethylthio]dibenzo[b,f]thiepin hydrochloride
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe aqueous mixture is extracted with an ether-toluene (1:1) mixture
- washThe combined extracts, successively, are washed well with water
- customdried
- filtrationfiltered
- customthe filtrate evaporated
- customleaving an orange oil
- customis recrystallized from a methanol-acetone-ether mixture
Sources & evidence
- ORD record
- ord-e1b425fcbac44df6a55d43bfd0f0d48a
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04775682
Reaction notes
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