Dimethyl-p-toluidine → 6-Bromo-4-chloro-3-methanesulfonyl-2-methyl-quinoline

HRID 13652

反応式

HRID 13652 の反応式
[Br: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>[Br: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]2[Cl:30]

参加物

5

反応物 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 178432088HCID 178432088、化合物

生成物 1

HCID 120016236-Bromo-4-chloro-3-methanesulfonyl-2-methyl-quinoline収率 18%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
20 °C

実験手順

6-Bromo-3-methanesulfonyl-2-methyl-quinolin-4-ol (example C.1) (6 g, 19 mmol) and N,N-dimethyl-p-toluidine (5.5 mL, 38 mmol) were dissolved in toluene (60 mL) and heated under argon to reflux. The phosphorous oxychloride (1.9 mL, 20.9 mL) was added and heating at reflux continued for 6.5 h. The product precipitated spontaneously upon cooling to 20° C., the crystals were filtered off and washed with little toluene. One obtained 4.19 g (66%) of light brown crystals. Since the product is somewhat soluble in toluene, the mother liquor was extracted with 3 N HCl (2×), sat. NaCl (2×). The residue was purified by chromatography on silica gel in dichloromethane. One obtained 1.17 g (18%) of additional material. MS: m/z=333/335 (M).

後処理

  1. temperatureheated under argon
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureat reflux
  5. customThe product precipitated spontaneously
  6. filtrationthe crystals were filtered off
  7. washwashed with little toluene
  8. customOne obtained 4.19 g (66%) of light brown crystals
  9. extractionthe mother liquor was extracted with 3 N HCl (2×), sat. NaCl (2×)
  10. customThe residue was purified by chromatography on silica gel in dichloromethane

出典と根拠

ORDレコード
ord-85758e9ad35f4e1f90481e2fa98a2d49
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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