Methanol → N-(3-Amino-2,2-dimethylpropyl)-1-amino-1,1-dimethyl-2-butanone oxime

HRID 47158

反応式

HRID 47158 の反応式
[CH3:1][C:2]([CH3:7])([CH2:5][NH2:6])[CH2:3][NH2:4].Cl[C:9]([CH3:15])([CH3:14])[CH:10]([N:12]=[O:13])[CH3:11].O.[CH3:17]O>>[NH2:4][CH2:3][C:2]([CH3:7])([CH3:1])[CH2:5][NH:6][C:9]([CH3:15])([CH3:14])[C:10](=[N:12][OH:13])[CH2:11][CH3:17]

参加物

5

反応物 4

HCID 887MethanolHCID 962WaterHCID 817702,2-Dimethyl-1,3-propanediamineHCID 108663862-Chloro-2-methyl-3-nitrosobutane

生成物 1

HCID 87946981N-(3-Amino-2,2-dimethylpropyl)-1-amino-1,1-dimethyl-2-butanone oxime

実験手順

To a solution of 2,2-dimethyl-1,3-propane diamine (69 g, 0.75 mole) in dry methanol (100 mL), 3-chloro-3-methyl-2-nitrosobutane (20.55 g, 0.15 mole, Example 1) was added in portions at 0° C. over a period of 2 hours. The reaction mixture was then stirred at room temperature for 20 hours. The solvent was removed under reduced pressure to give a paste. Water (50 mL) was added, and the solution was cooled in an ice bath. The solution was filtered and the filtrate was adjusted to pH 10-11 by the addition of sodium hydroxide. The solution was cooled again and filtered. The filtrate was concentrated under reduced pressure to a paste and then extracted with ether repeatedly (10×50 mL). The combined ether solution was concentrated to give an oil which was recrystallized twice from petroleum ether to yield the title A compound as a colorless crystalline solid (20.0 g), m.p. 58-60° C. 1H NMR [CDCl3]: δ0.85 (s, 6H, C—Me2), 1.28 (s, 6H, N—CMe2), 1.9 (s, 3H, N═CMe), 2.2 (s, 2H, NCH2) and 2.6 (s, 2H, N—CH2).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customto give a paste
  3. temperaturethe solution was cooled in an ice bath
  4. filtrationThe solution was filtered
  5. additionthe filtrate was adjusted to pH 10-11 by the addition of sodium hydroxide
  6. temperatureThe solution was cooled again
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a paste
  9. extractionextracted with ether repeatedly (10×50 mL)
  10. concentrationThe combined ether solution was concentrated
  11. customto give an oil which
  12. customwas recrystallized twice from petroleum ether

出典と根拠

ORDレコード
ord-74d13327b7ce47cb8e1cfe09732eb00d
出典データセット
uspto-grants-2004_03
特許番号
US06699458B2

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