1,3-Benzodioxole-5-carboxaldehyde, 7-methoxy- → 2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamide

HRID 1386033ノート

反応式

HRID 1386033 の反応式
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9].C([Li])CCC.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]2[O:35][CH2:34][O:33][C:32]=12)[CH:28]=[O:29].[Cl-].[NH4+]>O1CCCC1>[OH:29][CH:28]([C:27]1[CH:26]=[C:25]([O:24][CH3:23])[C:32]2[O:33][CH2:34][O:35][C:31]=2[CH:30]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:8]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:17])(=[O:9])=[O:10]

参加物

6

反応物 4

HCID 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-HCID 25517Ammonium ChlorideHCID 87657Benzenesulfono-o-toluidideHCID 178418339Butyllithium

生成物 1

HCID 186155802-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamide収率 48.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-72 °C

実験手順

To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C. a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure.

後処理

  1. additionwas added
  2. stirringthe mixture was stirred
  3. temperaturewarmed to 0° C. over 1.5 hours
  4. customthe organic phase was decanted
  5. customThe solvent was evaporated in vacuo
  6. washwashed with saturated sodium bicarbonate and brine solutions
  7. dry with materialThe solution was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give a syrup which
  11. customwas chromatographed on 500 g silica gel
  12. washeluted with a mixture of ethyl acetate and hexane (35:65)
  13. concentrationThe appropriate fractions were concentrated in vacuo
  14. customcrystallized
  15. customgiving a solid, 4.15 g, 48.6% yield, mp 155-158° C

出典と根拠

ORDレコード
ord-ce3ed88267ef4360b752d9cc6dc47d72
出典データセット
uspto-grants-2001_07
特許番号
US06265399B1

反応ノート

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