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

HRID 13653

반응식

HRID 13653 반응식
[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]

참가 물질

5

반응물 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 178432192HCID 178432192, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-02a1067405be4f21a8572dc3c61a0744
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728142B2

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