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

HRID 1701753ノート

反応式

HRID 1701753 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 79372,6-Lutidine溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e90b1e38589b4d55afb1b370f7848d61
出典データセット
uspto-grants-1980_03
特許番号
US04195090

反応ノート

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