Benzenesulfonyl chloride → HCID 58107388, compound

HRID 873672Notes

Reaction equation

HRID 873672 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-48e70d57e6784fd380abefd8b9c8d24b
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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