4-Nitrobenzenesulfonyl chloride → N-(1-Methylethyl)-N-[2-(1-methylethylamino)ethyl]-4-nitrobenzene sulfonamide

HRID 978805Notes

Reaction equation

HRID 978805 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:14]([NH:17][CH2:18][CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)Cl>[CH3:15][CH:14]([N:17]([CH2:18][CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11])[CH3:16]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 77628N,N'-Diisopropylethylenediamine

Product 1

HCID 13913711N-(1-Methylethyl)-N-[2-(1-methylethylamino)ethyl]-4-nitrobenzene sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

p-Nitrobenzenesulfonyl chloride (22.1 g, 0.1 mole) in methylene chloride (150 ml) was added dropwise with stirring to N,N'-diisopropyl ethylene diamine (14.4 g, 0.1 mole) and triethylamine (10.1 g, 0.1 mole) in methylene chloride (400 ml). The reaction was stirred one hour at room temperature, washed with water and the solvent removed. The residue dissolved in diethyl ether precipitated the unwanted "bis" byproduct which was filtered and discarded. Chromatography of the filtrate on Dry Column Silica Gel (500 g) with ethyl acetate provided pure product free base as a gum (14.31 g). Conversion, using isopropanol/HCl, to the hydrochloride salt provided the title compound as the hydrochloride salt (14.85 g) m.r. 219°-222° C.

Workup

  1. washwashed with water
  2. customthe solvent removed
  3. dissolutionThe residue dissolved in diethyl ether
  4. customprecipitated the unwanted "bis" byproduct which
  5. filtrationwas filtered
  6. dry with materialChromatography of the filtrate on Dry Column Silica Gel (500 g) with ethyl acetate provided pure product free base as a gum (14.31 g)

Sources & evidence

ORD record
ord-eec9c512f4f64ce995e0622282cc8233
Source dataset
uspto-grants-1987_05
Patent number
US04665227

Reaction notes

Loading…