Pyridine → HCID 68841809, compound

HRID 2110561Notes

Reaction equation

HRID 2110561 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[N:13]1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[NH2:1][C:2]1[CH:7]=[C:6]([NH:13][S:20]([CH3:19])(=[O:22])=[O:21])[CH:5]=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 218887652,5-Diaminobenzenesulfonamide

Product 1

HCID 68841809HCID 68841809, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

2,5-Diamino-benzenesulfonamide (288 mg, 1.5 mol, prepared according to the procedure as described in Goldfarb A. R. et. al., J. Amer. Chem. Soc. 1943, 65, 738) in dichloromethane (5 mL) and pyridine (5 mL) at 0° C. was treated dropwise with methanesulfonyl chloride (119 μL, 1.5 mmol) over 3 minutes. The reaction mixture was warmed to 25° C. and stirred for 18 hours and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with methanol in dichloromethane to yield the title compound (68% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.21 (m, 1H), 7.45 (d, J=2.57 Hz, 1H), 7.29 (s, 2H), 7.13 (dd, J=8.64, 2.39 Hz, 1H), 6.78 (d, J=8.82 Hz, 1H), 5.80 (s, 1H), 3.39 (s, 1H), 2.87 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was chromatographed on silica gel
  3. washeluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-1cdbbb2a900c40c1ac9fc9714348c9c6
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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