N,N-Dimethyl-1,3-propanediamine → N-[3-(dimethylamino)propyl]-2-nitrobenzenesulfonamide

HRID 1869009Notes

Reaction equation

HRID 1869009 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].C(N(CC)CC)C.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25])([O-:17])=[O:16]>ClCCl>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][S:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N+:15]([O-:17])=[O:16])(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 4125491N-[3-(dimethylamino)propyl]-2-nitrobenzenesulfonamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N-dimethyl-1,3-diaminopropane (0.92 g) and triethylamine (0.95 mL) in dichloromethane (10 mL) was added 2-nitrobenzenesulfonyl chloride (1 g), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (1.26 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-2f7af85a409a4bbeb0361831b2498b14
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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