N,N-Dimethylethylenediamine → N-(2-Dimethylaminoethyl)-3,5-Dinitrobenzenesulfonamide Hydrochloride

HRID 330536Notes

Reaction equation

HRID 330536 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:13]([Cl:16])(=[O:15])=[O:14])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21]>O1CCCC1>[ClH:16].[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH:21][S:13]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 132348993,5-Dinitrobenzene-1-sulfonyl chloride

Product 1

HCID 14723797N-(2-Dimethylaminoethyl)-3,5-Dinitrobenzenesulfonamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3,5-dinitrobenzensulfonyl chloride (4.6 g, 17.3 mmol) in dry tetrahydrofuran (130 mL) was added oer 50 min. to a cooled, stirred solution of N,N-dimethyl ethylenediamine (4.0 mL, 34.6 mmol) in tetrahydrofuran (100 mL). After stirring at room temperature overnight, tetrahydrofuran was removed under reduced pressure and the residue flash chromatographed over silica gel. The sulfonamide (5.1 g) was eluted with 5% methanol- 95% chloroform and purified as the hydrochloride salt, mp 238°-40°.

Workup

  1. customtetrahydrofuran was removed under reduced pressure
  2. customthe residue flash chromatographed over silica gel
  3. washThe sulfonamide (5.1 g) was eluted with 5% methanol- 95% chloroform
  4. custompurified as the hydrochloride salt, mp 238°-40°

Sources & evidence

ORD record
ord-d4a9269ba7144394b35046f7cacc5a9a
Source dataset
uspto-grants-1990_01
Patent number
US04897423

Reaction notes

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