Water → (2-Methylsulfanyl-3-methoxybenzyl)-dimethylamine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]([CH3:9])[CH3:8].C([Li])CCC.[CH3:18][S:19]SC.O>C1COCC1.C(OCC)C>[CH3:18][S:19][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[CH:10][C:5]=1[CH2:6][N:7]([CH3:9])[CH3:8]Participants
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, 3-methoxy-N,N-dimethylbenzylamine (2.00 g, 12.1 mmol) was dissolved in anhydrous THF (20 mL) and cooled to 0° C. in an ice bath. 2.5M n-butyl lithium in hexanes (5.3 mL, 13.3 mmol) was added slowly, maintaining the temperature to below 5° C. The reaction was stirred at 0° C. for 2 b, then dimethyldisulfide (1.59 g, 13 mmol) was slowly added over 90 min, maintaining the temperature to below 5° C. The reaction mixture was stirred for 17 h, during which time the temperature was allowed to reach room temperature. Water (20 mL) and diethyl ether (30 mL) were added and the organic layer was separated and dried with MgSO4. After filtration, the crude solution was dissolved in ethyl acetate and absorbed in vacuo onto silica gel (1.5 g). This material was chromatographed on an ISCO CombiFlash Chromatography System to yield (2-methylsulfanyl-3-methoxybenzyl)-dimethyl-amine as a yellow oil (1.47 g, 57%).
Workup
- temperaturemaintaining the temperature to below 5° C
- temperaturemaintaining the temperature to below 5° C
- stirringThe reaction mixture was stirred for 17 h, during which time the temperature
- customto reach room temperature
- customthe organic layer was separated
- dry with materialdried with MgSO4
- filtrationAfter filtration
- dissolutionthe crude solution was dissolved in ethyl acetate
- customabsorbed in vacuo onto silica gel (1.5 g)
- customThis material was chromatographed on an ISCO CombiFlash Chromatography System
Sources & evidence
- ORD record
- ord-f0570f881ace4e65b07b8d7ba0532718
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119122B2
Reaction notes
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