Hydrochloric Acid → HCID 23371312, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][O:14][CH2:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[N:12]=2)=[CH:4][CH:3]=1.[C:24](=O)([O:27]C)[O:25][CH3:26].[H-].[Na+].Cl>O1CCCC1.O.CO>[CH3:26][O:25][C:24]([CH:15]([O:14][CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[S:9][CH:10]=1)[C:16]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17])=[O:27]Participants
Procedure
A solution of 9.8 g (0.03 mol) of 2-[2-(4-fluorophenyl)-4-thiazolylmethyloxy]acetophenone in 80 ml of tetrahydrofuran is added dropwise to 3.0 g (0.033 mol) of dimethyl carbonate and 0.8 g (0.033 mol) of sodium hydride in 20 ml of tetrahydrofuran at 60° C. with stirring under nitrogen, and the mixture is then stirred at 60° C. for 1 hour. After cooling, first 5 ml of methanol and then 500 ml of water are added, and the mixture is acidified with dilute hydrochloric acid and extracted with methyl tert-butyl ether. The organic phase is washed with sodium bicarbonate solution, dried and concentrated. The result is 10.8 g (93% yield) of ω-methoxycarbonyl-2-[2-(4-fluorophenyl)-4-thiazolylmethyloxy]acetophenone as an ocher solid of melting point 86°-89° C.
Workup
- stirringthe mixture is then stirred at 60° C. for 1 hour
- temperatureAfter cooling
- extractionextracted with methyl tert-butyl ether
- washThe organic phase is washed with sodium bicarbonate solution
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1755a54ddebf468ea41b5d169e214234
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05538940
Reaction notes
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