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

HRID 23397노트

반응식

HRID 23397 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 695460711H-Indole-3-sulfonic Acid Dimethylamide수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-859a7472f97a4bb0beef2e3b7dfa771a
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852726B2

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