Sodium hydride → 1H-Indole-3-sulfonic Acid Dimethylamide

HRID 23397ノート

反応式

HRID 23397 の反応式
CN([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])C.[H-].[Na+]>CN(C=O)C>[CH3:17][N:16]([CH3:18])[S:13]([C:12]1[C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][CH:4]=1)(=[O:15])=[O:14]

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 22574107C-[2-(dimethylamino-methyleneamino)-phenyl]-N,N-dimethyl-methanesulfonamide

生成物 1

HCID 695460711H-Indole-3-sulfonic Acid Dimethylamide収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

The crude product from Step 3 was dissolved in DMF (7 ml) and to this solution was added sodium hydride (60% in oil, 0.353 g, 8.82 mmole) in portions under a nitrogen atmosphere. After the initial bubbling subsided, the temperature was raised to 40° C. and left at that temperature overnight. Tlc analysis of the reaction mixture showed the presence of starting material and thus the temperature was raised to 60° C. and heated another 24 h. After cooling the reaction mixture was partitioned between 1.5 M HCl and ethyl acetate. The organic layer was separated and washed with bicarbonate solution, and then with brine. After drying over magnesium sulfate and filtration, the solvent was removed under reduced pressure to afford 0.547 g of the crude product. Purification by column chromatography (silica gel, 5:95 ethyl acetate:methylene chloride) afforded 0.437 g of the pure 1H-Indole-3-sulfonic acid dimethylamide (66% yield).

後処理

  1. customAfter the initial bubbling
  2. temperaturethus the temperature was raised to 60° C.
  3. temperatureheated another 24 h
  4. temperatureAfter cooling the reaction mixture
  5. customwas partitioned between 1.5 M HCl and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with bicarbonate solution
  8. dry with materialAfter drying over magnesium sulfate and filtration
  9. customthe solvent was removed under reduced pressure
  10. customto afford 0.547 g of the crude product
  11. customPurification by column chromatography (silica gel, 5:95 ethyl acetate:methylene chloride)

出典と根拠

ORDレコード
ord-859a7472f97a4bb0beef2e3b7dfa771a
出典データセット
uspto-grants-2005_02
特許番号
US06852726B2

反応ノート

読み込み中…