Triethylamine → 3-(Methylsulfanyl)-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

HRID 44275

반응식

HRID 44275 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(OCl)(C)(C)C.C([O:18][C:19](=O)[CH2:20][S:21][CH3:22])C.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:22][S:21][CH:20]1[C:9]2[C:2](=[CH:3][CH:4]=[C:5]([C:6]#[N:7])[CH:8]=2)[NH:1][C:19]1=[O:18]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 133964-AminobenzonitrileHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochlorite

생성물 1

HCID 123514903-(Methylsulfanyl)-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-78 °C

실험 절차

To a solution of 4-amino-benzonitrile (84.64 mmoles) in DCM (200 ml) under a nitrogen atmosphere, at −78° C., there is added, dropwise, tBuOCl (84.64 mmoles) dissolved in 20 ml of DCM and then, after 10 minutes, ethyl(methylsulphanyl)acetate (84.64 mmoles) dissolved in 20 ml of DCM is added dropwise to the reaction mixture. After stirring for one hour at −78° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is stirred at ambient temperature for one hour. Water is added and the phases are then separated. The organic phase is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The residue is taken up in ethyl ether and aq. 2M HCl solution is added. After stirring overnight, the yellow precipitate is filtered off and dried in vacuo to yield the title product, which is used directly in the next reaction.

후처리

  1. additionis added dropwise to the reaction mixture
  2. stirringThe reaction mixture is stirred at ambient temperature for one hour
  3. customthe phases are then separated
  4. washThe organic phase is washed with water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. additionaq. 2M HCl solution is added
  9. stirringAfter stirring overnight
  10. filtrationthe yellow precipitate is filtered off
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-5927259c609b482ea10f5450258020d5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541412B2

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