Thiophenol → N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-3-methoxy-1-propanamine

HRID 85566노트

반응식

HRID 85566 반응식
[O:1]=[S:2]1(=[O:28])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:4][CH2:3]1.C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[O:28]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][NH:10][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH2:6][CH2:7]1

참가 물질

6

반응물 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 68358023N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-N-(3-methoxypropyl)-2-nitrobenzenesulfonamide

생성물 1

HCID 62561927N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-3-methoxy-1-propanamine수율 87.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-N-(3-methoxypropyl)-2-nitrobenzenesulfonamide (0.510 g, 1.17 mmol) and thiophenol (0.387 g, 3.51 mmol) were combined in dry acetonitrile (10 mL). Potassium carbonate (0.647 g, 4.68 mmol) was added and the mixture was stirred at rt for 18 h. The mixture was diluted with ethyl acetate and filtered to remove unwanted solids. The crude filtrate was concentrated in vacuo, redissolved in methanol, and loaded onto a strong cation exchange resin cartridge to capture the desired product. Undesired materials were eluted from the cartridge with methanol, and then the desired material was released from the resin by elution with 2M ammonia in methanol. Concentration in vacuo gave a yellow oil (0.255 g, 87% yield). No further purification was performed and the mixture was carried forward to the next step. LCMS: m/z 251 (M+H+), 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.77 (quin, J=6.53 Hz, 2H) 2.13 (br. s., 2H) 2.62-2.68 (m, 2H) 2.68-2.75 (m, 4H) 2.93-3.11 (m, 8H) 3.32 (s, 3H) 3.44 (t, J=6.15 Hz, 2H).

후처리

  1. filtrationfiltered
  2. customto remove unwanted solids
  3. concentrationThe crude filtrate was concentrated in vacuo
  4. dissolutionredissolved in methanol
  5. washUndesired materials were eluted from the cartridge with methanol
  6. washthe desired material was released from the resin by elution with 2M ammonia in methanol
  7. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-63c9340ed26b4047916768ab37731d84
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846647B2

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