4-Toluenesulfonyl chloride → N-(6-chloropyridazin-3-yl)-4-methylbenzenesulfonamide

HRID 1162428Notes

Reaction equation

HRID 1162428 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 216436-Amino-3-chloropyridazine

Product 1

HCID 3153536N-(6-chloropyridazin-3-yl)-4-methylbenzenesulfonamideYield 26.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

6-Chloro-pyridazin-3-ylamine (7 g, 54 mmol) was taken up in pyridine (54 mL) and TsCl (11.34 g, 59 mmol) was added. The solution was heated at 80-90° C. for 24 h. The solution was concentrated and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine (2×50 mL), dried over sodium sulfate and concentrated. Purification by silica gel chromatography (ethyl acetate/hexane) afforded the title compound (4 g, 26%). 1H NMR (DMSO-d6, 300 MHz): δ 2.4 (s, 3H), 7.4 (d, 3H), 7.54 (d, 1H), 7.8 (m, 3H), 12.5 (br, 1H)

Workup

  1. concentrationThe solution was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine (2×50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b06ba0f796ae4489b224e481cbe31d89
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

Loading…