p-Toluenesulfonic acid → HCID 66558588, compound

HRID 1474466Notes

Reaction equation

HRID 1474466 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[CH2:16][CH2:15][CH2:14]/[C:13](=[C:18]3/[C:19](=[O:28])[NH:20][C:21]4[C:26]/3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)/[C:12]=2[NH:11][C:10]=1[CH3:29])=[O:8])[CH3:2].C(#N)C.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([OH:44])(=[O:43])=[O:42])=[CH:37][CH:36]=1>ClCCl>[C:35]1([CH3:45])[CH:36]=[CH:37][C:38]([S:41]([OH:44])(=[O:42])=[O:43])=[CH:39][CH:40]=1.[CH2:30]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[CH2:16][CH2:15][CH2:14]/[C:13](=[C:18]3/[C:19](=[O:28])[NH:20][C:21]4[C:26]/3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)/[C:12]=2[NH:11][C:10]=1[CH3:29])=[O:8])[CH3:31]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6342AcetonitrileHCID 569355771032265-57-8

Product 1

HCID 66558588HCID 66558588, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.25 g (10 mmol) (Z)—N-[2-(diethylamino)ethyl]-2-methyl-7-(1,2-dihydro-5-fluoro-2-oxo-3H-indol-3-ylidene)-4,5,6,7-tetrahydro-1H-indol-3-carboxamide was added to a mixture of 250 ml acetonitrile and 50 ml dichloromethane. The mixture was treated under ultrasonic sound to uniform dispersion. 2.21 g (13 mmol) p-toluenesulfonic acid was added and the solution was heated to reflux with stirring under nitrogen atmosphere. After reaction for 1 h, the resulting mixture was filtered while being hot, and the filtrate was concentrated at reduced pressure to dryness, added to 30 ml anhydrous ethanol and treated under ultrasonic sound to uniform dispersion. Then the solution was filtered, and the filter cake was dried at 40° C. under vacuum, to give the title compound as yellow solid (5.43 g, 9.1 mmol, yield 91%).

Workup

  1. additionThe mixture was treated under ultrasonic sound to uniform dispersion
  2. temperaturethe solution was heated
  3. temperatureto reflux
  4. customAfter reaction for 1 h
  5. filtrationthe resulting mixture was filtered
  6. concentrationthe filtrate was concentrated at reduced pressure to dryness
  7. additionadded to 30 ml anhydrous ethanol
  8. additiontreated under ultrasonic sound to uniform dispersion
  9. filtrationThen the solution was filtered
  10. customthe filter cake was dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-2a435371906f4b2ab76eb065bd29a41b
Source dataset
uspto-grants-2015_04
Patent number
US09018242B2

Reaction notes

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