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Dichloromethane → N-Methyl-N-phenyl-2-(3-trifluoromethyl-4-phenyl-5-isoxazolyloxy)acetamide

HRID 477389
ノート
印刷プレビュー

反応式

HRID 477389 の反応式
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](=[O:6])[CH2:4][OH:5].CC(C)([O-])C.[K+].[F:19][C:20]([F:34])([F:33])[C:21]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:24](Cl)[O:23][N:22]=1.C(Cl)Cl>C1COCC1>[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](=[O:6])[CH2:4][O:5][C:24]1[O:23][N:22]=[C:21]([C:20]([F:34])([F:33])[F:19])[C:25]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 57434772-hydroxy-N-methyl-N-phenylacetamideHCID 143710873-Trifluoromethyl-4-phenyl-5-chloroisoxazoleHCID 23665647Potassium tert-butoxide

生成物 1

HCID 14855465N-Methyl-N-phenyl-2-(3-trifluoromethyl-4-phenyl-5-isoxazolyloxy)acetamide収率 61.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

0.99 g (6.0 mmole) of N-methyl-N-phenyl-2-hydroxyacetamide was dissolved in THF (6 ml) and the solution was mixed with 0.75 g (6.0 mmole) of 90% potassium t-butoxide with ice cooling. The mixture was stirred for 30 minutes and then 1.24 g (5.0 mmole) of 3-trifluoromethyl-4-phenyl-5-chloroisoxazole was added dropwise to the mixture. After being stirred for 30 minutes, the mixture was refluxed for 24 hours. After cooling the reaction mixture, 60 ml of methylene chloride was added and the mixture was washed with a 5% solution of HCl and water. The methylene chloride phase was evaporated under reduced pressure and the residue was purified by chromatography on silica gel to give 1.15 g of colorless crystals. These were recrystallized from n-hexane to give 950 mg of the titled compound, yield 50.5%, m.p. 93.0°-94.0° C.

後処理

  1. stirringAfter being stirred for 30 minutes
  2. temperaturethe mixture was refluxed for 24 hours
  3. additionwas added
  4. washthe mixture was washed with a 5% solution of HCl and water
  5. customThe methylene chloride phase was evaporated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-12a55684be7d46a5b9a3bebeb88e07a2
出典データセット
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04888044

反応ノート

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