Benzenesulfonyl chloride → HCID 59848832, compound

HRID 1096502Notes

Reaction equation

HRID 1096502 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:6]([C:7]=32)[CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[O:1]=[C:2]1[C:8]2=[CH:9][N:10]([S:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:30])=[O:29])[C:11]3[CH:12]=[CH:13][CH:14]=[C:6]([C:7]=32)[CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 59848835HCID 59848835, compound

Product 1

HCID 59848832HCID 59848832, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Tert-Butyl 3-oxo-1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 17 (50 mg, 0.17 mmol), tetrabutylammonium hydrogensulfate (8 mg, 0.01 mmol) and benzenesulfonyl chloride (25 μl, 0.19 mmol) were dissolved in DCM (2 ml). 2.5 M NaOH (77 μl) was added. The mixture was stirred for 1 h at room temperature. The DCM phase was collected and washed with NaHCO3(sat.) and water. Evaporation gave a residue that was purified on silica 8-66% EtOAc in petroleum ether 45-60°. Obtained 42.4 mg of the title compound as a clear glass. MS (ESI+) m/z 371 [M+H-isobutene]+.

Workup

  1. customThe DCM phase was collected
  2. washwashed with NaHCO3(sat.) and water
  3. customEvaporation
  4. customgave a residue that
  5. customwas purified on silica 8-66% EtOAc in petroleum ether 45-60°

Sources & evidence

ORD record
ord-4c5dbe0f0c464fa585f099ae6a5283ec
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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