Acetic Acid → 2-Isopropylthio-3-(cyclohexanon-2-yloxy)-pyridine

HRID 1653627

反応式

HRID 1653627 の反応式
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[CH:9]([S:12][C:13]1[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][N:14]=1)([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CN(C)C=O.C(OCC)(=O)C>[CH:9]([S:12][C:13]1[C:18]([O:19][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2=[O:8])=[CH:17][CH:16]=[CH:15][N:14]=1)([CH3:11])[CH3:10]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 11430Potassium Carbonate3 回HCID 132032-Chlorocyclohexanone3 回HCID 199579323-Pyridinol, 2-[(1-methylethyl)thio]-

生成物 1

HCID 570183552-Isopropylthio-3-(cyclohexanon-2-yloxy)-pyridine収率 72.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

7.29 g of 2-chlorocyclohexanone are added at room temperature to a mixture of 8.4 g of 2-isopropylthio-3-hydroxypyridine and 7.6 g of potassium carbonate in 120 ml of dimethylformamide, and the mixture is stirred for one hour at 45°-50° C. After the addition of 1.46 g of 2-chlorocyclohexanone and 1.52 g of potassium carbonate and after 2 hours of a further analogous addition of 0.73 g of 2-chlorocyclohexanone and 0.76 g of potassium carbonate, the suspension is stirred for a further 3.5 hours at 45°-50° C. The resulting reaction solution is poured onto a mixture consisting of 200 ml of ice-water, 50 ml of 2N acetic acid and 100 ml of ethyl acetate, washed three times with 300 ml of ethyl acetate and 100 ml of saturated sodium chloride solution each time, dried over sodium sulfate and concentrated by evaporation. The residue is triturated with petroleum ether and filtered. 9.57 g of the desired ketone having a melting point of 106°-110° C. are obtained.

後処理

  1. stirringthe suspension is stirred for a further 3.5 hours at 45°-50° C
  2. customThe resulting reaction solution
  3. additionis poured onto a mixture
  4. washwashed three times with 300 ml of ethyl acetate and 100 ml of saturated sodium chloride solution each time
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue is triturated with petroleum ether
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-46014526f7844a69a3bd3795aa33ee8d
出典データセット
uspto-grants-1995_04
特許番号
US05403814

関連ノート

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