Ethylene carbonate → 2-{[2-(2-Dimethylaminoethoxy)-3-pyridinyl]oxy}ethanol

HRID 1958291

반응식

HRID 1958291 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]([CH3:19])[CH2:9][CH2:10][O:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1.C1(=O)O[CH2:23][CH2:22][O:21]1>CS(C)=O>[CH3:7][N:8]([CH3:19])[CH2:9][CH2:10][O:11][C:12]1[C:17]([O:18][CH2:23][CH2:22][OH:21])=[CH:16][CH:15]=[CH:14][N:13]=1

참가 물질

5

반응물 3

HCID 7303Ethylene carbonate2회HCID 11430Potassium CarbonateHCID 219089932-(2-Dimethylaminoethoxy)pyridin-3-ol

생성물 1

HCID 117083962-{[2-(2-Dimethylaminoethoxy)-3-pyridinyl]oxy}ethanol

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
58 °C

실험 절차

DMSO (17 L) and potassium carbonate (8.2 kg) were charged to the 100 L-glasslined reactor. The mixture was heated to 58° C. while stirring. 2-(2-Dimethylaminoethoxy)pyridin-3-ol (4.11 kg) was charged to the reactor during 25 minutes (gas evolution). The mixture was heated to 117° C. before the prepared ethylene carbonate solution was added through the manhood in portions. After 1 L ethylene carbonate solution was added IP-HPLC was taken to ensure that the title compound had started to form. The total addition of ethylene carbonate solution was made during 1 h 35 minutes. Temperature after the addition was 124° C. A HPLC sample was taken from the reaction mixture 10 minutes after finished addition. It showed 95% conversion to product. The reaction-mixture was allowed to cool to 70° C. before water (45 L) and sodium chloride (4.06 kg) was charged to the reactor. The mixture was then stirred for 20 minutes at 70° C. before cooled to RT. Ethyl acetate (137 L) was charged into a 328 L glass-lined reactor. The water mixture was transferred from the 100 L reactor to the 328 L reactor. The mixture was stirred for 25 minutes before the mechanical stirrer was turned off. After allowing the phases to separate for 40 minutes, the water-phase (65 L) was discharged. The mixture was heated to reflux and 102 L of ethyl acetate was distilled off. Toluene (72 L) was added and the mixture was heated to reflux again and 61 L of toluene/ethyl acetate was distilled off. The reaction mixture was then cooled to RT. The title compound was never isolated; it was directly used in Example 2C.

후처리

  1. additionwas added through the manhood in portions

출처 및 근거

ORD 기록
ord-5fb2fe759afd4d62a9dddf2eccfd9424
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410113B2

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