N,N-bis(3-aminopropyl)methylamine → N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine

HRID 68177

반응식

HRID 68177 반응식
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][N:19]([CH2:24][CH2:25][CH2:26][NH2:27])[CH2:20][CH2:21][CH2:22][NH2:23]>C1(C)C=CC=CC=1>[CH3:18][N:19]([CH2:24][CH2:25][CH2:26][NH:27][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1)[CH2:20][CH2:21][CH2:22][NH:23][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1

참가 물질

5

반응물 3

HCID 7777N,N-bis(3-aminopropyl)methylamineHCID 10340Sodium CarbonateHCID 949565-Fluoro-2-nitrotoluene

생성물 1

HCID 86731947N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To 5-fluoro-2-nitrotoluene (50.0 g, 0.32 mol) was added sodium carbonate (17.1 g, 0.16 mol) at 60° C. 3,3′-Diamino-N-methyldipropylamine (23.7 g, 0.16 mol) was then carefully added dropwise (exothermic reaction). The resulting mixture was heated at 100° C. for 12 hours. 100 ml toluene were added to the cooled reaction mixture causing the inorganic salts to precipitate, which were filtered off. The organic phase was then concentrated down under vacuum in a rotovap to afford the product as a residue in the form of a yellow orange oil. Yield: 52.5 g (78.4%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=1.71 (m, 4H); 2.18 (s, 3H); 2.40 (m, 4H); 2.55 (s, 6H); 3.17 (m, 4H); 6.45 (s, 2H); 6.48 (d, 2H); 7.08 (br., 2×NH); 7.92 (d, 2H).

후처리

  1. custom(exothermic reaction)
  2. customto precipitate
  3. filtrationwhich were filtered off
  4. concentrationThe organic phase was then concentrated down under vacuum in a rotovap
  5. customto afford the product as a residue in the form of a yellow orange oil

출처 및 근거

ORD 기록
ord-727ba28406384fee9d438a866f21cfd8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08821592B1

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