Dimethyl-p-toluidine → 4-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline

HRID 13653

反応式

HRID 13653 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:5]2O.CN(C)C1C=CC(C)=CC=1.P(Cl)(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[Cl:30][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=[C:7]([CH3:12])[C:6]=1[S:13]([CH3:16])(=[O:15])=[O:14]

参加物

5

反応物 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 178432192HCID 178432192、化合物

生成物 1

HCID 120016244-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline収率 78%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-ol (example C.2) (14.7 g, 40.5 mmol) and N,N-dimethyl-p-toluidine (11.7 mL, 81 mmol) were dissolved in toluene (150 mL) and heated under argon to reflux. Then phosphorous oxychloride (4.1 mL, 44.5 mmol) was added and heating at reflux continued for 9.5 h. The thick suspension became gradually a dark solution. The reaction mixture was allowed to cool and then extracted with dichloromethane (not soluble in toluene), cold 1 N HCl (2×), and sat. NaCl (2×). The product was crystallized from heptane/dichloromethane. One obtained 12 g (78%) of white crystals. MS: m/z=381 (M).

後処理

  1. temperatureheated under argon
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureat reflux
  5. temperatureto cool
  6. extractionextracted with dichloromethane (not soluble in toluene), cold 1 N HCl (2×), and sat. NaCl (2×)
  7. customThe product was crystallized from heptane/dichloromethane

出典と根拠

ORDレコード
ord-02a1067405be4f21a8572dc3c61a0744
出典データセット
uspto-grants-2010_06
特許番号
US07728142B2

関連ノート

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