Tert-Butyl nitrite → 3-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

HRID 397143

反応式

HRID 397143 の反応式
N(OC(C)(C)C)=O.[O:8]1[CH2:12][CH2:11][C:10]([C:13]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:14]=2N)=[N:9]1.[CH3:21][S:22]SC>[Cu]>[CH3:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:14]([S:22][CH3:21])[C:13]=1[C:10]1[CH2:11][CH2:12][O:8][N:9]=1

参加物

5

反応物 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl Disulfide2 回HCID 97940062-(4,5-Dihydroisoxazol-3-yl)-3-methylaniline

生成物 1

HCID 108783423-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

試薬・触媒・溶媒 1

HCID 23978Copper触媒

反応条件

温度
60 °C

実験手順

19.5 g (170 mmol) of tert-butyl nitrite and 20 g of copper powder are initially charged in 30 ml of dimethyl disulfide, and a solution of 20 g (114 mmol) of 2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline in 100 ml of dimethyl disulfide is added dropwise at from 50 to 55° C. The mixture is then stirred at 60° C. for 1.5 hours. For work-up, the solid is filtered off with suction and the solution is diluted with methylene chloride and extracted with dilute hydrochloric acid. The organic phase is washed with saturated aqueous NaHCO3 solution, dried over sodium sulfate, filtered off and concentrated. Excess dimethyl disulfide is removed under oil pump vacuum.

後処理

  1. filtrationFor work-up, the solid is filtered off with suction
  2. additionthe solution is diluted with methylene chloride
  3. extractionextracted with dilute hydrochloric acid
  4. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. customExcess dimethyl disulfide is removed under oil pump vacuum

出典と根拠

ORDレコード
ord-de56d8249e9b41bcbeafc32e540f4321
出典データセット
uspto-grants-2003_08
特許番号
US06608209B2

関連ノート

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