Methanol → Methyl 2-(methylamino)-2-phenylacetate
Reaction equation
S(Cl)(Cl)=O.[CH3:5][NH:6][CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9].[CH3:17]O>>[CH3:5][NH:6][CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([O:10][CH3:17])=[O:9]Participants
4
Procedure
6.63 mL of thionyl chloride are slowly added to a solution of 1.5 g of 2-methylamino-2-phenylacetic acid in 100 mL of methanol. The mixture is heterogenous and becomes limpid after two hours stirring. The mixture is stirred for 48 h at rt then the solvent is evaporated to dryness. The crude product is diluted with an aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phases are washed with water then brine, and dried over magnesium sulfate, filtered and evaporated to provide the desired product, which is used as such for the next step.
Workup
- stirringThe mixture is stirred for 48 h at rt
- customthe solvent is evaporated to dryness
- additionThe crude product is diluted with an aqueous sodium bicarbonate solution
- extractionextracted with ethyl acetate
- washThe organic phases are washed with water
- dry with materialbrine, and dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-4d338209c4ef4259957412b8a23e8f73
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383608B2
Reaction notes
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