4-Chloro-3-nitrobenzenesulfonamide → 4-(4-Methylpiperazin-1-ylamino)-3-nitrobenzenesulfonamide

HRID 706860Notes

Reaction equation

HRID 706860 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.Cl.[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([NH2:24])[CH2:20][CH2:19]1.CN(C)CCN(C)C>O1CCOCC1>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([NH:24][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 1982214-Methylpiperazin-1-ylamine dihydrochloride hydrate

Product 1

HCID 47377414-(4-Methylpiperazin-1-ylamino)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 50 mL round-bottomed flask was charged with 4-chloro-3-nitrobenzenesulfonamide (1 g, 4.23 mmol), 4-methylpiperazin-1-amine dihydrochloride (1 g, 5.32 mmol), and N1,N1,N2,N2-tetramethylethane-1,2-diamine (3 mL, 20.01 mmol) in dioxane (10 mL). The reaction mixture was refluxed for 12 hours. After this time, the reaction mixture was cooled to room temperature, the salt filtered off via a Buchner funnel, and the solvent removed in vacuo. The crude product was added to a silica gel column (Analogix, SF65-200g) and purified by eluting with 0-5% methanol in dichloromethane.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. filtrationthe salt filtered off via a Buchner funnel
  3. customthe solvent removed in vacuo
  4. additionThe crude product was added to a silica gel column (Analogix, SF65-200g)
  5. custompurified
  6. washby eluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-825071fa8f3242048a042563b5ed0413
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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