Benzenesulfonyl chloride → HCID 58107388, compound

HRID 1810200Notes

Reaction equation

HRID 1810200 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:21])([CH3:20])[C:5]([N:7]1[CH2:19][CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH2:8]1)=[O:6].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1([S:28]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]3[CH2:18][CH2:19][N:7]([C:5](=[O:6])[C:4]([CH3:21])([CH3:20])[CH3:3])[CH2:8][C:9]2=3)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 44771633HCID 44771633, compound

Product 1

HCID 58107388HCID 58107388, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a well-agitated suspension of sodium hydroxide (0.81 g, 20.2 mmol) in methylene chloride (10 mL) is added 2,2-dimethyl-1-(1,3,4,9-tetrahydro-pyrido[3,4-b]indol-2-yl)-propan-1-one (2.3 g, 8.98 mmol). The reaction mixture is stirred for 15 min, and then benzenesulfonyl chloride (1.89 g, 10.7 mmol) is added. The solution is stirred at room temperature for 1 h. The reaction is diluted with methylene chloride, washed with water then a saturated sodium chloride solution, dried with sodium sulfate and concentrated in vacuo. Purification by silica gel chromatography (50% ethyl acetate-hexane) provides 2.0 g (56.2%) of the title compound as a white solid.

Workup

  1. stirringThe solution is stirred at room temperature for 1 h
  2. washwashed with water
  3. dry with materiala saturated sodium chloride solution, dried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1d003302aee9426280498cff741a51ff
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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