Butylamine → HCID 13732573, compound

HRID 1731544Notes

Reaction equation

HRID 1731544 reaction equation
C(N)CCC.CN(C)C=[C:9]([C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[S:10][CH2:11][CH2:12][N:13]1[C:21](=O)C2C(=CC=CC=2)C1=O>C(O)C>[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([C:9]2[S:10][CH2:11][CH2:12][NH:13][CH:21]=2)=[O:32])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 8007ButylamineHCID 54405536HCID 54405536, compound

Product 1

HCID 13732573HCID 13732573, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.527 kg (34.5M) n-Butylamine is added to a stirred solution of 23 1 ethanol and 4.58 kg (11,5M) 2-[2-(2-dimethylamino-1-(4-fluorobenzoyl)vinylthio)ethyl]-1,3-isoindoledione under nitrogen atomosphere and the solution is heated at reflux temperature for 24 hours. The reaction mixture is cooled and stirred at 10° for 3 hours. The crude product is collected by filtration, washed several times with ethanol and ether and dried. The crude product is dissolved at 90° in dimethylformamide and the solution is filtered through a heated funnel. A solid begins to form and the resulting suspension is stirred at room temperature overnight, filtered, washed with ether and dried. M.P. 212°-214° ; IR (N): NH 3100, C=O 1580; NMR (DMSO): 7.02-7.55 (m, 6H), 3.48 (m, 2H), 2.77 (m, 2H).

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationThe crude product is collected by filtration
  5. washwashed several times with ethanol and ether
  6. customdried
  7. dissolutionThe crude product is dissolved at 90° in dimethylformamide
  8. filtrationthe solution is filtered through a heated funnel
  9. customto form
  10. stirringthe resulting suspension is stirred at room temperature overnight
  11. filtrationfiltered
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-e88011fb2df64555930bc28b0f6abad5
Source dataset
uspto-grants-1986_11
Patent number
US04622322

Reaction notes

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