Dimethyl Sulfide → N,N-Diethyl-4-methoxy-2-(methylthio)benzamide
Reaction equation
N[C@H](C(O)=O)C[SeH].[Li]CCCC.CN(C)CCN(C)C.[CH2:21]([N:23]([CH2:34][CH3:35])[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[CH3:22].[CH3:36][S:37]C>C1COCC1>[CH2:34]([N:23]([CH2:21][CH3:22])[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[S:37][CH3:36])[CH3:35]Participants
Procedure
Sec-BuLi (1.4 M in cyclohexane, 11.34 mL, 15 mmol) was carefully added to a mixture of N,N,N′,N′-tetramethylethane-1,2-diamine (2.2 mL, 15 mmol) in anhydrous THF at −78° C. N,N-Diethyl-4-methoxybenzamide (3 g, 14.4 mmol) dissolved in 5 mL of anhydrous THF was added dropwise to the reaction mixture which was allowed to stir for 1 h. Dimethyl sulfide (2.5 mL, 28.8 mmol) was then added to the reaction. After stirring for 15 min, the cooling bath was removed and the mixture was stirred overnight. The reaction was diluted with ethyl acetate and washed with a solution of saturated sodium bicarbonate, water and then brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 20 to 80% ethyl acetate in hexanes to obtain the product as a light yellow oil. Yield=2.51 g. MS (M+H)+ 254.
Workup
- additionwas added dropwise to the reaction mixture which
- stirringAfter stirring for 15 min
- customthe cooling bath was removed
- stirringthe mixture was stirred overnight
- additionThe reaction was diluted with ethyl acetate
- washwashed with a solution of saturated sodium bicarbonate, water
- dry with materialThe organic layer was then dried with sodium sulfate
- concentrationconcentrated
- custompurified by flash chromatography
Sources & evidence
- ORD record
- ord-30dadc65744642a58f7f34e3f021c1fa
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858785B2
Reaction notes
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