Hydrogen Bromide → HCID 178419729, compound

HRID 840893Notes

Reaction equation

HRID 840893 reaction equation
C([N:4]1[C:12]2[CH:11]=[C:10]3[C:13](=O)[C:14](=[O:16])[NH:15][C:9]3=[CH:8][C:7]=2[CH2:6][CH2:5]1)(=O)C.[CH:18]1[C:23]([NH:24][NH2:25])=[CH:22][CH:21]=[C:20]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:19]=1.Cl.[BrH:31]>O.CCO>[BrH:31].[O:16]=[C:14]1[NH:15][C:9]2=[CH:8][C:7]3[CH2:6][CH2:5][NH:4][C:12]=3[CH:11]=[C:10]2[C:13]1=[N:25][NH:24][C:23]1[CH:22]=[CH:21][C:20]([S:26]([NH2:29])(=[O:27])=[O:28])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21956269HCID 21956269, compound

Product 1

HCID 178419729HCID 178419729, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.10 g (0.44 mmol) of 5-acetyl-1,5,6,7-tetrahydro-pyrrolo[2,3-f]indole-2,3-dione in 3 mL of conc. HBr was heated to 100° C. for 18 h. The mixture was cooled to ambient temperature, diluted with 10 mL of water and filtered. The filtrate was concentrated in vacuo and added to a solution of 0.05 g (0.2 mmol) 4-sulfonamidophenylhydrazine hydrochloride in 5 mL of EtOH. The mixture was heated to 80° C. for 1 h and cooled to ambient tempurature. The resulting solid was collected by vacuum filtration, washed with water and dried in a vacuum oven at 70° C. to afford the title compound as a tan solid (0.026 g, 17%): mp>250° C.; 1H NMR (DMSO-d6): δ3.17 (t, J=7.8 Hz, 2H), 3.69 (t, J=7.8 Hz, 2H), 6.96 (s, 1H), 7.25 (s, 2H), 7.52 (s, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.77 (d, J=8.8 Hz, 2H), 10.65 (bs, 2H), 11.24 (s, 1H), 12.73 (s, 1H); APCI−MS: m/z 356 (M−H)−. Anal. Calcd for C16H15N5O3S.0.9HBr.0.5H2O: C, 43.75; H, 3.88; N, 15.94; S, 7.30. Found: C, 44.01; H, 4.14; N, 15.70; S, 7.12.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. temperatureThe mixture was heated to 80° C. for 1 h
  4. temperaturecooled to ambient tempurature
  5. filtrationThe resulting solid was collected by vacuum filtration
  6. washwashed with water
  7. customdried in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-bd2020a8624140c2946cda8e29ccb61f
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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