Methyl vinyl sulfone → HCID 22036162, compound

HRID 1789656Notes

Reaction equation

HRID 1789656 reaction equation
[CH3:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([N:17]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:38][S:39]([CH:42]=[CH2:43])(=[O:41])=[O:40].[H-].[Na+]>CN(C=O)C>[CH3:38][S:39]([CH2:42][CH2:43][N:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:37][CH:36]=1)[C:8]1[CH:9]=[CH:10][C:11]([S:14]([N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)(=[O:15])=[O:16])=[CH:12][CH:13]=1)(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 22036179HCID 22036179, compound

Product 1

HCID 22036162HCID 22036162, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[(4-methyl-benzyl)-amino]-[N,N-bis(4-methoxy-benzyl)]-benzenesulfonamide (1.03 g, 2.6 mmol) was dissolved in 6 mL of DMF at room temperature, to which methylvinyl sulfone (0.175 mL, 2.0 mmol) and sodium hydride (95%, 60 mg, 2.4 mmol) were added. The reaction was stirred at room temperature for 1.5 h, partitioned between ethyl acetate and water, dried over MgSO4 and purified by column chromatography, eluting with 1:4 acetone/hexane, to provide 935 mg of 4-[(2-methylsulfonyl-ethyl)-(4-methyl-benzyl)-amino]-[N,N-bis(4-methoxy-benzyl)]-benzenesulfonamide.

Workup

  1. additionwere added
  2. custompartitioned between ethyl acetate and water
  3. dry with materialdried over MgSO4
  4. custompurified by column chromatography
  5. washeluting with 1:4 acetone/hexane

Sources & evidence

ORD record
ord-3f973467b88445e8a5090f809444380e
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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