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

HRID 505859Notes

Reaction equation

HRID 505859 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>C1(C)C=CC=CC=1>[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 8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 257 mg (1.02 mmol) N,N-diallyl 4-methylbenzenesulfonamide (prepared according to S. Varray, R. Lazaro., J. Matinez, F. Lamaty, Organometallics 2003, 22, 2426-2435) and 19 mg (0.03 mmol) [RuCl2(ImH2Mes)((4-chloro-2-trifluoromethyl-8-quinolinyl)methylene)] in 5 ml toluene was stirred at 110° C. To monitor the conversion and selectivity, 0.2-ml samples were taken were after 1 h and 4 h. Each sample was filtered over a silica gel pad, the filtrate was evaporated to dryness and analyzed by GC (column: DB-1701; injector: 260° C.; detector: 260°; oven: 70 to 250° C./5° C. per min; carrier gas: H2 (60 kPa); retention times: 15.5 min N,N-diallyl 4-methylbenzenesulfonamide, 24.5 min 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole, 25.5 min 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole). After 1 h (98% conversion), 96% of the title compound and 2% of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole and after 4 h (100% conversion) 92% of the title compound and 8% of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole were formed. 1H-NMR of 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole (300 MHz, C6D6): 2.43 (s, 3H); 4.12 (s, 4H); 5.65 (s, 2H); 7.32 (d, J=8.3 Hz, 2H); 7.73 (d, J=8.3 Hz, 2H). 1H-NMR of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole (300 MHz, C6D6): 2.40-2.55 (m, 2H); 2.43 (s, 3H); 3.48 (t, J=8.9 Hz, 2H); 5.10-5.15 (m, 1H); 8.35-8.40 (m, 1H); 7.32 (d, J=8.3 Hz, 2H); 7.67 (d, J=8.3 Hz, 2H).

Workup

  1. filtrationEach sample was filtered over a silica gel pad
  2. customthe filtrate was evaporated to dryness
  3. customanalyzed by GC (column: DB-1701; injector: 260° C.; detector: 260°; oven: 70 to 250° C./5° C. per min; carrier gas: H2 (60 kPa); retention times: 15.5 min N,N-diallyl 4-methylbenzenesulfonamide, 24.5 min 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole, 25.5 min 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole)
  4. waitAfter 1 h (98% conversion), 96% of the title compound and 2% of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole
  5. waitafter 4 h (100% conversion) 92% of the title compound

Sources & evidence

ORD record
ord-cf478e71530a49cfaac5c2a02b804e05
Source dataset
uspto-grants-2010_08
Patent number
US07781586B2

Reaction notes

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