Phosgene → 5-{[(6-Methylpyridin-3-yl)oxy]methyl}-3-(propan-2-yl)-1,3-oxazolidin-2-one

HRID 1701753노트

반응식

HRID 1701753 반응식
[C:1](Cl)(Cl)=[O:2].[OH:5][CH:6]([CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[CH2:7][O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1>C1(C)C=CC=CC=1.O1CCOCC1.N1C(C)=CC=CC=1C>[CH:18]([N:17]1[CH2:16][CH:6]([CH2:7][O:8][C:9]2[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[O:5][C:1]1=[O:2])([CH3:20])[CH3:19]

참가 물질

6

반응물 2

HCID 6371PhosgeneHCID 204834671-[(6-Methylpyridin-3-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

생성물 1

HCID 204834455-{[(6-Methylpyridin-3-yl)oxy]methyl}-3-(propan-2-yl)-1,3-oxazolidin-2-one

시약·촉매·용매 3

HCID 1140Toluene용매HCID 79372,6-Lutidine용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 10 g of phosgene in 40 ml of toluene is added dropwise at 5°-10° C. to 15.6 g of 3-(2'-hydroxy-3'-isopropylamino-propoxy)-6-methyl-pyridine, dissolved in 75 ml of dioxane, in the presence of 8 ml of 2,6-lutidine, whilst stirring. The reaction mixture is stirred overnight at room temperature and is then evaporated in vacuo. The evaporation residue is rendered alkaline with a little concentrated sodium hydroxide solution and is extracted with 200 ml of ethyl acetate. The organic phase is evaporated, initially at approx. 20 mm Hg and then at 0.1 mm Hg/60° C. bath temperature. Approx. 50 ml of ether are added to the residue which remains, giving crystalline 3-isopropyl-5-[(6-methylpyridin-3-yloxy)methyl]-oxazolidin-2-one of melting point 86°-88° C.

후처리

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. customis then evaporated in vacuo
  3. extractionis extracted with 200 ml of ethyl acetate
  4. customThe organic phase is evaporated, initially at approx. 20 mm Hg
  5. customat 0.1 mm Hg/60° C. bath temperature
  6. additionApprox. 50 ml of ether are added to the residue which

출처 및 근거

ORD 기록
ord-e90b1e38589b4d55afb1b370f7848d61
출처 데이터셋
uspto-grants-1980_03
특허 번호
US04195090

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