3,4-Dichlorophenyl isocyanate → Ethyl 5-(3,4-dichlorophenylcarbamoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

HRID 1808383ノート

反応式

HRID 1808383 の反応式
[O:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:2]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][C:17]=1[Cl:25]>C1(C)C=CC=CC=1>[Cl:25][C:17]1[CH:18]=[C:19]([NH:22][C:23]([N:6]2[CH2:7][CH2:8][C:9]3[O:1][N:2]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]=3[CH2:5]2)=[O:24])[CH:20]=[CH:21][C:16]=1[Cl:15]

参加物

4

反応物 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 44558551Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

生成物 1

HCID 59483856Ethyl 5-(3,4-dichlorophenylcarbamoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate (A-06) (for synthesis see above) (0.5 g, 2.55 mmol) was dissolved in toluene (25 ml), and 1,2-dichloro-4-isocyanatobenzene (0.48 g, 2.55 mmol) was added. The reaction mixture was refluxed for 2 h. Toluene was removed in vacuo, the residue was taken up in ethyl acetate and sat. sodium hydrogen carbonate solution, and the phases were separated. The aqueous phase was extracted with ethyl acetate, and then the combined organic phases were washed with sat. sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. Purification of the crude product was carried out by column chromatography (silica gel, diethyl ether/hexane 2:1). Yield: 1.2 g (>99%)

後処理

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customToluene was removed in vacuo
  3. customsat. sodium hydrogen carbonate solution, and the phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe combined organic phases were washed with sat. sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product

出典と根拠

ORDレコード
ord-ae5d6781a2ce430cb1048eb6003dfb05
出典データセット
uspto-grants-2013_01
特許番号
US08357717B2

反応ノート

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