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

HRID 475935Notes

Reaction equation

HRID 475935 reaction equation
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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1548619899034c13b4f320e55472390f
Source dataset
uspto-grants-2014_01
Patent number
US08637658B2

Reaction notes

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