Dichloromethane → N-(3-dimethylamino-6-methoxyphenyl)acetamide

HRID 475935ノート

反応式

HRID 475935 の反応式
NC1C=[C:4]([NH:10]C(=O)C)[C:5]([O:8][CH3:9])=[CH:6]C=1.[CH:14]([N:17]([CH:20]([CH3:22])[CH3:21])[CH2:18]C)(C)C.COS([O:28][CH3:29])(=O)=O.[OH-].[Na+].[CH2:32](Cl)Cl>>[CH3:14][N:17]([CH3:18])[C:20]1[CH:22]=[C:4]([NH:10][C:29](=[O:28])[CH3:32])[C:5]([O:8][CH3:9])=[CH:6][CH:21]=1

参加物

6

反応物 5

HCID 6344Dichloromethane2 回HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 267867n-(5-Amino-2-methoxyphenyl)acetamide

生成物 1

HCID 67430069N-(3-dimethylamino-6-methoxyphenyl)acetamide収率 50%

実験手順

N-(3-amino-6-methoxyphenyl)acetamide 25 (1.0 gm, 0.0055 moles) was dissolved in 30 ml DCM at room temperature under argon with stirring. Diisopropylethylamine (4.83 ml, 0.028 moles) and dimethylsulfate (2.36 ml, 0.025 moles) were added. After stirring at room temperature for 8 hours, 30 ml DCM and 40 ml 0.3 N NaOH were added. The mixture was partitioned and the aqueous layer was washed with three 30 ml portions of DCM. The combined organic extract was washed with saturated NaCl, dried over MgSO4, filtered, and concentrated to give N-(3-dimethylamino-6-methoxyphenyl)acetamide 26 (0.57 gm, 50%). 1H NMR (CDCl3) δ 8.01, 1H, m; 7.75, 1H, br s; 6.79, 1H, d; 6.43, 1H, dd; 3.82, 3H, s; 2.89, 6H, s, 2.19; 3H, s.

後処理

  1. stirringAfter stirring at room temperature for 8 hours
  2. customThe mixture was partitioned
  3. washthe aqueous layer was washed with three 30 ml portions of DCM
  4. extractionThe combined organic extract
  5. washwas washed with saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-1548619899034c13b4f320e55472390f
出典データセット
uspto-grants-2014_01
特許番号
US08637658B2

反応ノート

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