Sodium Hydroxide → N-[3-(4,5,7-trifluorobenzothiazol-2-yl)-1-thioxopropyl]-N-methylglycine
Reaction equation
C([O:3][C:4](=[O:24])[CH2:5][N:6]([C:8](=[S:23])[CH2:9][CH2:10][C:11]1[S:12][C:13]2[C:19]([F:20])=[CH:18][C:17]([F:21])=[C:16]([F:22])[C:14]=2[N:15]=1)[CH3:7])C.[OH-].[Na+]>O.O1CCOCC1>[F:22][C:16]1[C:14]2[N:15]=[C:11]([CH2:10][CH2:9][C:8]([N:6]([CH3:7])[CH2:5][C:4]([OH:24])=[O:3])=[S:23])[S:12][C:13]=2[C:19]([F:20])=[CH:18][C:17]=1[F:21]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-[3-(4,5,7-trifluorobenzothiazol-2-yl)-1-thioxopropyl]-N-methylglycine ethyl ester (190 mg, 0.5 mmol) in a mixture of water (3 ml) and dioxane (6 ml) was added dropwise 2N sodium hydroxide (0.6 mmol) with stirring under ice-cooling and the mixture was stirred for 1 hour at room temperature, then diluted with water and washed with ether. The aqueous phase was acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried and then evaporated to yield a residue, which was crystallized from isopropyl ether to give N-[3-(4,5,7-trifluorobenzothiazol-2-yl)-1-thioxopropyl]-N-methylglycine (155 mg, 88%) as a pale brown powder.
Workup
- temperaturecooling
- stirringthe mixture was stirred for 1 hour at room temperature
- washwashed with ether
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- customdried
- customevaporated
- customto yield a residue, which
- customwas crystallized from isopropyl ether
Sources & evidence
- ORD record
- ord-05f3068abbb5490aaf9543cc2d8bd1ac
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05700819
Reaction notes
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