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

HRID 2075565ノート

反応式

HRID 2075565 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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) yo yield 6.1 g of the desired product (87%). Calculated mass=272. Observed mass=273

後処理

  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) yo yield 6.1 g of the desired product (87%)

出典と根拠

ORDレコード
ord-cc1fa6c487944874ad40e18963b0f2cd
出典データセット
uspto-grants-2011_04
特許番号
US07919617B2

反応ノート

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