Sodium Hydroxide → HCID 21416160, compound
Reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:4]=2[CH2:3]1.[N:22]1([CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][O:32][C:31]2=[O:35])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[OH-].[Na+]>>[F:13][C:10]1[CH:11]=[CH:12][C:7]2[S:6][C:5]3[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:4]=3[CH2:3][CH:2]([N:25]3[CH2:26][CH2:27][N:22]([CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][O:32][C:31]4=[O:35])[CH2:23][CH2:24]3)[C:8]=2[CH:9]=1Participants
Procedure
11.6 G. of 10-chloro-8-fluoro-10,11-dihydro-3-trifluoromethyl-dibenzo[b,f]thiepin are treated with 27.8 g. of 3-[2-(1-piperazinyl)-ethyl]-2-oxazolidinone and stirred at 115°-120° C. for 10 minutes. The mixture is cooled and treated with 2N sodium hydroxide. The product separating as an oil is extracted with ether. The organic solution is washed to neutrality with water and shaken out with a dilute, aqueous methanesulfonic acid solution. The aqueous solution is made alkaline with sodium hydroxide and extracted with ether. The ether solution is washed with water, dried over magnesium sulfate and concentrated, whereby there is obtained 3-{2-[4-(8-fluoro-10,11-dihydro-3-trifluoromethyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone as a yellow oil which is converted into the dimethanesulfonate (melting point 149°-151° C.) by the addition of methansulfonic acid.
Workup
- temperatureThe mixture is cooled
- customThe product separating as an oil
- extractionis extracted with ether
- washThe organic solution is washed
- extractionextracted with ether
- washThe ether solution is washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-10b33774a9884fa2b96abdb5243f6400
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04044010
Reaction notes
Loading…