Phosphorus oxychloride → HCID 14537098, 화합물

HRID 232242

반응식

HRID 232242 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

HCID 14537098HCID 14537098, 화합물수율 73%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-826fe5a2e558404282a8b1efcedba498
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851536

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