Phosphorus oxychloride → HCID 14537098、化合物

HRID 232242

反応式

HRID 232242 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6](O)=O.P(Cl)(Cl)([Cl:14])=O.O=[C:18]1[CH2:23][CH2:22][CH:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:20][CH2:19]1>>[CH3:27][O:26][C:24]([CH:21]1[CH2:22][CH2:23][C:18]2[C:19](=[C:6]([Cl:14])[C:5]3[C:4]([N:11]=2)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[CH2:20]1)=[O:25]

参加物

4

反応物 3

HCID 24813Phosphorus oxychlorideHCID 666462-Amino-4-chlorobenzoic acidHCID 226643Methyl 4-oxocyclohexanecarboxylate

生成物 1

HCID 14537098HCID 14537098、化合物収率 73%

実験手順

To a slurry of 16.5 g (0.096 mol) of 4-chloroanthranilic acid and 166 ml of phosphorous oxychloride is added portionwise 15 g (0.096 mol) of methyl 4-ketocyclohexane carboxylate. The reaction mixture is refluxed for 3 h, cooled, and concentrated in vacuo. The residue is dissolved in methylene chloride and poured into an ice-NH4OH mixture. The aqueous phase is separated and extracted with methylene chloride. The combined organic phases are dried over Na2SO4 and concentrated in vacuo. The residue is triturated with ethyl ether to give 21.7 g (73%) of the title compound: IR (KBr) 1730, 1605, 1580, and 1550 cm-1 ; NMR (DMSO-d6) δ 8.14-8.08 (m, 1H), 8.0-7.96 (m, 1H), 7.70-7.64 (m, 1H), 3.70 (s, 3H), 3.30-3,16 (m, 1H), 3.12-2.96 (m, 4H), 2.32-2.20 (m, 1H), and 2.04-1.86 (m, 1H).

後処理

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in methylene chloride
  5. additionpoured into an ice-NH4OH mixture
  6. customThe aqueous phase is separated
  7. extractionextracted with methylene chloride
  8. dry with materialThe combined organic phases are dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue is triturated with ethyl ether

出典と根拠

ORDレコード
ord-826fe5a2e558404282a8b1efcedba498
出典データセット
uspto-grants-1989_07
特許番号
US04851536

関連ノート

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