Pyridine → HCID 131710862, compound

HRID 441592Notes

Reaction equation

HRID 441592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[CH:4][CH:3]=1.[CH2:10]([C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([S:21]([NH:24][CH3:25])(=[O:23])=[O:22])=[C:14]([NH:26][CH2:27][CH2:28][CH3:29])[C:13]=1[N+:30]([O-:32])=[O:31])[CH3:11].N1C=CC=CC=1>ClCCl>[CH2:10]([C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([S:21]([N:24]([S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:25])(=[O:23])=[O:22])=[C:14]([NH:26][CH2:27][CH2:28][CH3:29])[C:13]=1[N+:30]([O-:32])=[O:31])[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 110844654-ChlorobenzenesulfenylchlorideHCID 88816106HCID 88816106, compound

Product 1

HCID 131710862HCID 131710862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2.2 g (0.012 mol) sample of p-chlorophenylsulfenyl chloride was added dropwise to a cooled (-5° C. to 0° C.) solution of 3.5 g (0.1 mol) 4-ethylpropylamino-N-methyl-3,5-dinitrobenzenesulfonamide and 1.1 g (0.014 mol) pyridine in 25 ml dichloromethane. The reaction was stirred for 20 minutes and then diluted with 50 ml dichloromethane, washed with water, washed with aqueous sodium bicarbonate solution, and dried over magnesium sulfate. The dichloromethane was then evaporated under reduced pressure to give a solid residue. Recrystallization from ethanol gave the product as red-orange plates, m.p. 89°-91° C. Elemental analysis for C18H21ClN4O6S2 showed: % S, calc. 13.1, found 13.3; % Cl, calc. 7.3, found 7.8.

Workup

  1. washwashed with water
  2. washwashed with aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customThe dichloromethane was then evaporated under reduced pressure
  5. customto give a solid residue
  6. customRecrystallization from ethanol
  7. customgave the product as red-orange plates, m.p. 89°-91° C

Sources & evidence

ORD record
ord-de8259e0ee274f85aa6f51b5723aa10f
Source dataset
uspto-grants-1977_08
Patent number
US04041159

Reaction notes

Loading…