ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Hydrochloric Acid → 3-(5-(3,5-Dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)aniline

HRID 1958653
ノート
印刷プレビュー

反応式

HRID 1958653 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Sn](Cl)Cl.Cl>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:25])([F:24])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 593556103-(5-(3,5-Dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)nitrobenzene

生成物 1

HCID 593556813-(5-(3,5-Dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)aniline収率 58.4%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-(3,5-dichloro-phenyl)-3-(3-nitro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (15.0 g, 37 mmol) (Example I2) in isopropanol (120 ml) was added tin(II) chloride (25 g, 133 mmol). The mixture was cooled to 0° C. and aqueous hydrochloric acid (concentrated) (23 ml) was added slowly at 0° C. The reaction mixture was heated to 80° C. for 2 hours. Then ⅓ of the total volume of isopropanol was evaporated. Water (100 ml) was added to the mixture and aqueous sodium hydroxide (4N) was added to adjust the pH to 8-9. The aqueous phase was extracted three times with ethyl acetate (200 ml). The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1) to give 3-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenylamine (8.1 g, 58% yield). 1H-NMR (CDCl3, 400 MHz): 7.56 (m, 2H), 7.43 (m, 1H), 7.20 (t, 1H), 7.05 (m, 1H), 6.97 (m, 1H), 6.78 (m, 1H), 4.08 (d, 1H), 3.8 (s, 1H), 3.68 (d, 1H).

後処理

  1. temperatureThe reaction mixture was heated to 80° C. for 2 hours
  2. customThen ⅓ of the total volume of isopropanol was evaporated
  3. additionWater (100 ml) was added to the mixture and aqueous sodium hydroxide (4N)
  4. additionwas added
  5. extractionThe aqueous phase was extracted three times with ethyl acetate (200 ml)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-9c405e637a944415ba74380c69dcb6c2
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410145B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート