Thionyl Chloride → 3-Ethyl-pentanoic acid (2,6-dimethyl-4-morpholin-4-yl-phenyl)-amide

HRID 1867304

반응식

HRID 1867304 반응식
[CH2:1]([CH:3]([CH2:8][CH3:9])[CH2:4][C:5]([OH:7])=O)[CH3:2].S(Cl)(Cl)=O.[CH3:14][C:15]1[CH:20]=[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[C:17]([CH3:27])[C:16]=1[NH2:28].C(=O)(O)[O-].[Na+].[Cl-].[Na+].O.O>C(#N)C>[CH3:14][C:15]1[CH:20]=[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[C:17]([CH3:27])[C:16]=1[NH:28][C:5](=[O:7])[CH2:4][CH:3]([CH2:1][CH3:2])[CH2:8][CH3:9]

참가 물질

6

반응물 4

HCID 24386Thionyl ChlorideHCID 1344603-Ethylpentanoic acidHCID 230094142,6-Dimethyl-4-morpholin-4-yl-phenylamineHCID 131727349Sodium bicarbonate brine water

생성물 1

HCID 116668733-Ethyl-pentanoic acid (2,6-dimethyl-4-morpholin-4-yl-phenyl)-amide수율 30.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
110 °C

실험 절차

3-Ethylpentanoic acid (0.79 g) and thionyl chloride (0.44 mL) were mixed in acetonitrile (10 mL) and heated to 110° C. for 5 minutes in a sealed microwave process vial. 2,6-Dimethyl-4-morpholin-4-yl-phenylamine (1.25 g) dissolved in acetonitrile (10 mL) was added to the reaction mixture and heated to 150° C. for 15 minutes in a sealed microwave process vial. Saturated aqueous sodium bicarbonate/brine/water (1:1:1, 50 mL) was added to the crude mixture and it was extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was recrystallized from hot toluene, and the product was collected by filtration, washed with cold toluene and dried in vacuo to furnish 0.59 g (30% yield) of the title compound as an off-white solid. LC-MS (m/z) 319 (MH+); tR=2.04, (UV, ELSD) 98%, 99%. 1H NMR (500 MHz, DMSO-d6): 0.87 (t, 6H), 1.35 (qui, 4H), 1.76 (m, 1H), 2.07 (s, 6H), 2.20 (d, 2H), 3.05 (t, 4H), 3.71 (t, 4H), 6.62 (s, 2H), 8.94 (s, 1H).

후처리

  1. additionwas added to the reaction mixture
  2. temperatureheated to 150° C. for 15 minutes in a sealed microwave process vial
  3. extractionwas extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was recrystallized from hot toluene
  7. filtrationthe product was collected by filtration
  8. washwashed with cold toluene
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-a5c7167ee23441f3a83864384ae58641
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632835B2

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