Dichloromethane → HCID 14851919, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([OH:24])[N:9]=1.S(Cl)(Cl)=O.[CH2:29](Cl)Cl>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([O:24][CH3:29])[N:9]=1Participants
Procedure
A mixture of 0.435 g (1 mmol) of rac-6-(2-fluorophenyl)-4-hydroxy-8-iodo-1-methyl-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepine, 3 ml of thionyl chloride and 20 ml of methylene chloride was stirred at room temperature for 2 hours. After evaporation under reduced pressure, the residue was dissolved in 20 ml of methanol and the solution was :reated with 3 ml of triethylamine. After heating on the steam bath for 5 minutes, the mixture was evaporated to dryness and the residue was partitioned between methylene chloride and aqueous sodium bicarbonate solution. The organic layer was dried and evaporated and the residue was crystallized from ethyl acetate to yield colorless crystals of rac-6-(2-fluorophenyl)-8-iodo-4-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepine with m.p. 240°-242°. The analytical sample was recrystallized from methanol/ethyl acetate and had m.p. 243°-244°.
Workup
- customAfter evaporation under reduced pressure
- dissolutionthe residue was dissolved in 20 ml of methanol
- temperatureAfter heating on the steam bath for 5 minutes
- customthe mixture was evaporated to dryness
- customthe residue was partitioned between methylene chloride and aqueous sodium bicarbonate solution
- customThe organic layer was dried
- customevaporated
- customthe residue was crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-fa2f57ee8ce84ce9ac20da679e46fd44
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04959361
Reaction notes
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