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

HRID 629595

Reaction equation

HRID 629595 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 mixture of 4-chloro-3-nitrobenzenesulfonamide (1 g), 4-methylpiperazin-1-amine dihydrochloride (1 g) and N1,N1,N2,N2-tetramethylethane-1,2-diamine (3 mL) in dioxane (10 mL) was refluxed for 12 hours, cooled to ambient temperature and filtered. The filtrate was added to a silica gel column (Analogix, SF65-200g) and purified by eluting with 1-5% methanol/dichloromethane).

Workup

  1. temperaturewas refluxed for 12 hours
  2. filtrationfiltered
  3. additionThe filtrate was added to a silica gel column (Analogix, SF65-200g)
  4. custompurified
  5. washby eluting with 1-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-24a237a09b1b41e5b7b6af1501ecb3dd
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Linked notes

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