Potassium Carbonate → 4-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamide
Reaction equation
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][C:32]=1[CH2:33][CH2:34][S:35][Si](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:25]([N:27]([CH3:29])[CH3:28])=[O:26]>CO>[SH:35][CH2:34][CH2:33][C:32]1[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:28])[CH3:29])=[O:26])=[CH:23][C:22]=1[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Citric acid monohydrate (110 mg, 0.523 mmol) and potassium carbonate (52.8 mg, 0.382 mmol) were added to a solution of 3,N,N-trimethyl-4-(2-triphenylsilanylsulfanyl-ethyl)-benzamide (767 mg, 1.59 mmol) in MeOH (27 ml) at room temperature, and the mixture was stirred for one hour. The reaction mixture was concentrated under reduced pressure, and the residue was then dissolved in dichloromethane. The organic layer was washed with water, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 4-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamide (351 mg, 99%).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was then dissolved in dichloromethane
- washThe organic layer was washed with water
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)
Sources & evidence
- ORD record
- ord-bc18df286931403eb7a34e78b47ac7c7
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169254B2
Reaction notes
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