Triethylamine → N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

HRID 2353540Notes

Reaction equation

HRID 2353540 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:14])[C:8]([O:12][CH3:13])=[C:9]([NH2:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:14][C:7]1[C:8]([O:12][CH3:13])=[C:9]([NH:11][S:23]([CH3:22])(=[O:25])=[O:24])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 41772354-tert-Butyl-2,6-diaminoanisole

Product 1

HCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. customTo an oven dried 250 mL round bottom flask
  2. additionwas added
  3. additionwas added
  4. temperaturethen warmed to room temperature
  5. stirringstirring for an additional 2 h
  6. customthe layers separated
  7. washThe aqueous layer was washed twice more with 50 mL dichloromethane
  8. dry with materialthe combined organic layers were dried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. customto afford a crude oil that
  11. customwas purified by flash chromatography (silica gel, 1:1 EtOAc:Hex)

Sources & evidence

ORD record
ord-f271ef8d29a446349c9c82b78a999e9e
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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