Resorcinol, 5-methyl-, monohydrate → 3-(5-Isoquinolinylsulfonyloxy)-5-methylphenol

HRID 442967ノート

反応式

HRID 442967 の反応式
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[CH:11]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([S:21](Cl)(=[O:23])=[O:22])[C:15]=2[CH:14]=[CH:13][N:12]=1>C([O-])(O)=O.[Na+].C(OCC)C.O>[CH:11]1[C:20]2[C:15](=[C:16]([S:21]([O:5][C:4]3[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=3)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1

参加物

6

反応物 2

HCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 33716555-Isoquinolinesulfonyl chloride

生成物 1

HCID 227225063-(5-Isoquinolinylsulfonyloxy)-5-methylphenol収率 37%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Orcinol monohydrate (1.42 g, 10.0 mmol) and 5-isoquinolinesulfonyl chloride (2.64 g, 10.0 mmol), as prepared in the preceding step, were mixed in saturated aqueous NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was triturated from ether/hexane to give the title compound as a pale yellow solid (1.15 g, 37%). 1H-NMR (300 MHz, CDCl3) δ 9.67 (s, 1H), 9.60 (s, 1H), 8.86 (d, J=6.1 Hz, 1H), 8.63 (d, J=8.2 Hz, 1H), 8.37 (t, J=6.1 Hz, 2H), 7.86 (t, J=7.8 Hz, 1H), 6.46 (s, 1H), 6.23 (s, 1H), 5.97 (s, 1H), 2.08 (s, 3H).

後処理

  1. extractionextracted into ethyl acetate (3×50 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was triturated from ether/hexane

出典と根拠

ORDレコード
ord-d110b810f03740afb536171e5faaa59f
出典データセット
uspto-grants-1999_04
特許番号
US05891909

反応ノート

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