Dichloromethane → 2-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

HRID 1444675Notes

Reaction equation

HRID 1444675 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].ClCCl.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 218887652,5-Diaminobenzenesulfonamide

Product 1

HCID 249506572-Amino-5-[(methylsulfonyl)amino]benzenesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,5-diamino-benzenesulfonamide (0.288 g, 0.0015 mol, 1 eq.), dichloromethane (5 mL), and pyridine (5 mL) was stirred at 0° C. Methanesulfonyl chloride (119 μL, 0.0015 mol, 1 eq.) was added dropwise over 3 minutes. The reaction mixture was warmed to 25° and stirred for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel using a step gradient of 0-4% methanol in dichloromethane to yield 2-amino-5-[(methylsulfonyl)amino]benzenesulfonamide (68% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.87 (s, 3H) 3.39 (s, 1H) 5.80 (s, 1H) 6.78 (d, J=8.82 Hz, 1H) 7.13 (dd, J=8.64, 2.39 Hz, 1H) 7.29 (s, 2H) 7.45 (d, J=2.57 Hz, 1H) 9.21 (m, 1H), MS (ESI+) m/z=266 (M+H)+.

Workup

  1. temperatureThe reaction mixture was warmed to 25°
  2. stirringstirred for 18 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe residue was chromatographed on silica gel using a step gradient of 0-4% methanol in dichloromethane

Sources & evidence

ORD record
ord-3734b924fcd849bda6a28bdd56b6612c
Source dataset
uspto-grants-2010_02
Patent number
US07662958B2

Reaction notes

Loading…