Benzenesulfonyl cyanide → 2-Benzenesulfonyl-5-chloropyridine

HRID 1953794Notes

Reaction equation

HRID 1953794 reaction equation
C(O[CH:5]=[C:6]([Cl:9])[CH:7]=[CH2:8])(=O)C.[C:10]1([S:16]([C:19]#[N:20])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[C:10]1([S:16]([C:19]2[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][N:20]=2)(=[O:17])=[O:18])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 10313279Benzenesulfonyl cyanideHCID 542547732-Chloro-1,3-butadienyl acetate

Product 1

HCID 101989402-Benzenesulfonyl-5-chloropyridineYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Toluene (60 ml) was heated to 100° C. Thereto was added dropwise a solution of 39.6 g of 2-chloro-1,3-butadienyl acetate and 30.0 g of benzenesulfonyl cyanide (purity:82%) in 60 ml of toluene over 30 minutes. The reaction mixture was stirred at 100° C. for 7 hours and then concentrated under reduced pressure. The crystals obtained were washed with 150 ml of toluene which was cooled to 0° C. and dried under reduced pressure using a vacuum pump to give 31.9 g of 2-benzenesulfonyl-5-chloropyridine (yield 86%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crystals obtained
  3. washwere washed with 150 ml of toluene which
  4. temperaturewas cooled to 0° C.
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7161f44f07f746ab8ace7d0ab41eb31a
Source dataset
uspto-grants-2000_09
Patent number
US06118005

Reaction notes

Loading…