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

HRID 475935노트

반응식

HRID 475935 반응식
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

참가 물질

6

반응물 5

HCID 6344Dichloromethane2회HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 267867n-(5-Amino-2-methoxyphenyl)acetamide

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1548619899034c13b4f320e55472390f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637658B2

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