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

HRID 1035870

Reaction equation

HRID 1035870 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, SF65-200 g) 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
  5. customSF65-200 g) and purified
  6. washby eluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-17071ac8d1b14bcea7eb326a207c1607
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Linked notes

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