Reaktion #685890

Reaktionsgleichung

sodium bicarbonate

triethylamine

5-tert-butyl-2-methoxy-benzene-1,3-diamine

methylsulfonyl chloride

→

desired product

Ausbeute 87.1%

N-(3-Amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

Ausbeute 87.1%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo an oven dried 250 mL round bottom flask
2. 2
   workup.ADDITIONwas added
3. 3
   workup.ADDITIONwas added
4. 4
   Temperaturthen warmed to room temperature
5. 5
   workup.STIRRINGstirring for an additional 2 h
6. 6
   Sonstigethe layers separated
7. 7
   WaschenThe aqueous layer was washed twice more with 50 mL dichloromethane
8. 8
   Trocknenthe combined organic layers were dried over magnesium sulfate
9. 9
   Einengenconcentrated under vacuum
10. 10
    Sonstigeto afford a crude oil that
11. 11
    Sonstigewas purified by flash chromatography (silica gel, 1:1 EtOAc:Hex)

Vorschrift

To an oven dried 250 mL round bottom flask containing 5.0 g (25.73 mmol) 5-tert-butyl-2-methoxy-benzene-1,3-diamine, 150 mL DCM was added. The reaction mixture was cooled to 0° C. after which triethylamine (5.0 mL, 36.0 mmol) was added followed by the drop wise addition of methylsulfonyl chloride (1.99 mL, 25.7 mmol). The reaction was allowed to stir at 0° C. for 30 min. then warmed to room temperature stirring for an additional 2 h. The reaction mixture was poured over saturated solution of sodium bicarbonate (100 mL) and the layers separated. The aqueous layer was washed twice more with 50 mL dichloromethane and the combined organic layers were dried over magnesium sulfate and concentrated under vacuum to afford a crude oil that was purified by flash chromatography (silica gel, 1:1 EtOAc:Hex) to yield 6.1 g of the desired product (87%). Calculated mass=272. Observed mass=273

Quelle