Hexanal → N-(tert-butyl)-N-hexylideneamine

HRID 76244

반응식

HRID 76244 반응식
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[CH:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>C(Cl)Cl>[C:1]([N:5]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6184HexanalHCID 6385Tert-ButylamineHCID 24083Sulfuric acid magnesium salt (1:1)

생성물 1

HCID 11829679N-(tert-butyl)-N-hexylideneamine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To t-butyl amine (5.25 mL, 50.0 mmol) and MgSO4 (2 g) in CH2Cl2 (10 mL) at room temperature was added slowly hexanal (6.0 mL, 50 mmol) under N2 at room temperature. The reaction became exothermic halfway through the addition so an ice bath was briefly used to control the reaction rate and avoid boiling off the solvent or amine. After the addition was complete, the reaction was stirred at room temperature for 2 h, filtered through celite under a stream of N2 and washed with 20 mL dry CH2Cl2. The solvent was evaporated to give a pale yellow liquid. 1H NMR (300 MHz, CDCl3) δ 0.87-0.91 (m, 3H), 1.17 (s, 9H), 1.25-1.35 (m, 4H), 1.45-1.55 (m, 2H), 2.23 (m, 2H), 7.59 (t, 1H).

후처리

  1. additionthrough the addition so an ice bath
  2. additionAfter the addition
  3. filtrationfiltered through celite under a stream of N2
  4. washwashed with 20 mL dry CH2Cl2
  5. customThe solvent was evaporated
  6. customto give a pale yellow liquid

출처 및 근거

ORD 기록
ord-2881d6ca74c5407e8f5f4edf29f409b2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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