Dichloromethane → tert-Butyl-bis(2-methoxyethyl)amine

HRID 1067902

反応式

HRID 1067902 の反応式
S([O:6][CH3:7])(OC)(=O)=O.[C:8]([N:12]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:14]O)([CH3:11])([CH3:10])[CH3:9].Cl[CH2:20]Cl.[OH-].[Na+]>>[C:8]([N:12]([CH2:13][CH2:14][O:6][CH3:7])[CH2:16][CH2:17][O:18][CH3:20])([CH3:11])([CH3:10])[CH3:9]

参加物

5

反応物 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 62430tert-Butyldiethanolamine

生成物 1

HCID 21195179tert-Butyl-bis(2-methoxyethyl)amine

実験手順

Dimethyl sulfate (50.45 g, 0.4 mol) was added dropwise to a vigorously stirred mixture of N-tert-butyldiethanolamine (16.13 g, 0.1 mol), dichloromethane (100 ml) tetrabutylammonium bromide (3.22 g, 10 mmol) and 50% aqueous sodium hydroxide (80 g, 1 mol at 30-40° C. The stirring was continued for 1 h after the addition was completed. The organic solution was separated and the aqueous layer was extracted with dichltromethane (25 ml). The organic solutions were combined. GC analysis showed a mixture of mono- and diethylated product. The methylation was repeated using the same amounts of reagents as described above. The dichloromethane solution after the second workup was stirred with concentrated aqueous ammonia (50 ml) for 1 h at room temperature, separated, dried over anhydrous magnesium sulfate and the product was isolated by distillation to yield 17.00 g, (90%), bp 42-44° C./0.1 mm/Hg; 1H NMR (CDCl3) δ1.60 (s, 9H, CH3), 2.70 (t, J=6.0 Hz, 4H, CH2), 3.35 (s, 6H, CH3), 3.37 (t, J=6.0 Hz, 4H, CH2)

後処理

  1. additionafter the addition
  2. customThe organic solution was separated
  3. extractionthe aqueous layer was extracted with dichltromethane (25 ml)
  4. additiona mixture of mono- and
  5. customseparated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe product was isolated by distillation
  8. customto yield 17.00 g, (90%), bp 42-44° C./0.1 mm/Hg

出典と根拠

ORDレコード
ord-c433b436a9914ce9a4a6708d85669cb3
出典データセット
uspto-grants-2001_06
特許番号
US06248885B1

関連ノート

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