Phosphorus oxychloride → HCID 22674092、化合物

HRID 1173120ノート

反応式

HRID 1173120 の反応式
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[N:16][CH:15]=[CH:14]3)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:22]C1C=CC=C(C(OO)=O)C=1.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[Cl:22][C:17]1[C:18]2[C:13](=[CH:12][C:11]([NH:10][S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:21])=[CH:6][CH:5]=3)(=[O:8])=[O:9])=[CH:20][CH:19]=2)[CH:14]=[CH:15][N:16]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 70297m-Chloroperbenzoic acidHCID 22674130HCID 22674130、化合物

生成物 1

HCID 22674092HCID 22674092、化合物収率 49.4%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

6-(4-Toluenesulfonylamino) isoquinoline (3.0 g, Production Example 21b) was dissolved in chloroform (100 ml). Under ice-cooling, m-chloroperbenzoic acid (2.57 g) was added thereto, followed by stirring at room temperature overnight. The solvent was evaporated, and the resulting crystals were washed with diethyl ether, collected by filtration and dried, to give pale yellow crystals. The crystals were suspended in chloroform (83 ml) and phosphorous oxychloride (19 ml) was added thereto, followed by heating under reflux for 5 hours. After cooling, the solvent was evaporated. The residue was basified by adding an aqueous saturated sodium bicarbonate in an ice bath, and then the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column, to give crude crystals of the title compound (1.630 g, 49.40%). The crystals were recrystallized from ethanol, to give the title compound as colorless crystals.

後処理

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated
  3. washthe resulting crystals were washed with diethyl ether
  4. filtrationcollected by filtration
  5. customdried
  6. customto give pale yellow crystals
  7. temperatureby heating
  8. temperatureunder reflux for 5 hours
  9. temperatureAfter cooling
  10. customthe solvent was evaporated
  11. additionby adding an aqueous saturated sodium bicarbonate in an ice bath
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe extract was washed with brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customthe solvent was evaporated
  16. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-7ee22318b0f94471ba67c7a764b9271f
出典データセット
uspto-grants-2010_11
特許番号
US07834049B2

反応ノート

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