Reaction equation
[OH-:1].[Na+].C[O:4][C:5]1[CH:21]=[CH:20][C:8]2[S:9][C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#N)[C:11]=3[CH2:12][CH2:13][C:7]=2[CH:6]=1.[OH2:22]>C(O)COCCO>[OH:4][C:5]1[CH:21]=[CH:20][C:8]2[S:9][C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:22])=[O:1])[C:11]=3[CH2:12][CH2:13][C:7]=2[CH:6]=1Participants
Conditions
- Temperature
- 200 °C
Procedure
An amount of 2.2 g of sodium hydroxide was dissolved in 30 ml of diethylene glycol by application of heat and to the mixture was added 2.2 g of 2-methoxy-9-cyano-10,11-dihydrodibenzo[b,f]thiepin and the resulting mixture was stirred at 200° C. for 16 hours. After cooling, to the mixture was added water and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate. This extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and freed of the solvent to obtain the residue. This residue was recrystallized from benzene to afford 1.1 g (46%) of 2-hydroxy-9-carboxy-10,11-dihydrodibenzo[b,f]thiepin as brown crystals having a melting point of 210°-211° C.
Workup
- temperatureof heat and to the mixture
- temperatureAfter cooling, to the mixture
- extractionthe mixture was extracted with ethyl acetate
- extractionextracted with ethyl acetate
- washThis extract was washed with saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customto obtain the residue
- customThis residue was recrystallized from benzene
Sources & evidence
- ORD record
- ord-6e6294addf104eb6be44c1ed484b8cc5
- Source dataset
- uspto-grants-1979_08
- Patent number
- US04166127
Linked notes
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