N,N-diallyl-4-methylbenzenesulfonamide → HCID 11746243, compound

HRID 505860Notes

Reaction equation

HRID 505860 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])C=C>ClCCl>[C:11]1([CH3:14])[CH:10]=[CH:9][C:8]([S:5]([N:4]2[CH:1]=[CH:17][CH2:16][CH2:15]2)(=[O:6])=[O:7])=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 351447N,N-diallyl-4-methylbenzenesulfonamide

Product 1

HCID 11746243HCID 11746243, compoundYield 0.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Barbasiewicz et al. (Organometallics, published on Web Jun. 17, 2006), a solution of 88 mg (0.35 mmol) N,N-diallyl 4-methylbenzenesulfonamide and 11.2 mg (0.018 mmol) [RuCl2(ImH2Mes)(8-quinolinylmethylene)] in 17.5 ml dichloromethane was stirred at room temperature. To monitor the conversion and selectivity, 0.2-ml samples were taken were after 4 h and 24 h. Each sample was filtered over a silica gel pad, the filtrate was evaporated to dryness and analyzed by GC as described in Example 12. After 4 h (2% conversion), 0.6% of the title compound and 0.3% of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole and after 24 h (3% conversion) 1.5% of the title compound and 0.5% of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole were formed.

Workup

  1. filtrationEach sample was filtered over a silica gel pad
  2. customthe filtrate was evaporated to dryness
  3. waitAfter 4 h (2% conversion), 0.6% of the title compound and 0.3% of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole
  4. waitafter 24 h (3% conversion) 1.5% of the title compound

Sources & evidence

ORD record
ord-895a14e159884b28b02109e8474a8893
Source dataset
uspto-grants-2010_08
Patent number
US07781586B2

Reaction notes

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