2-Nitrobenzenesulfonyl chloride → HCID 58244793, compound

HRID 1408310Notes

Reaction equation

HRID 1408310 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH3:8])[CH2:5][CH2:6][NH2:7].[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18](Cl)(=[O:20])=[O:19])([O-:11])=[O:10]>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][N:4]([CH3:8])[CH2:5][CH2:6][NH:7][S:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N+:9]([O-:11])=[O:10])(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 430288N-Methyl-2,2'-diaminodiethylamine

Product 1

HCID 58244793HCID 58244793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N1-(2-aminoethyl)-N1-methylethane-1,2-diamine (10.58 g, 90 mmoles) in DCM (350 mL) was added slowly a solution of 2-nitrobenzene-1-sulfonyl chloride dissolved in DCM (50 mL). After 2 h at RT, the reaction mixture (RM) was washed with water, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel with a gradient of methanol in DCM (0 to 10%), yielding to 6.9 g of N-(2-((2-aminoethyl)(methyl)-amino)ethyl)-2-nitrobenzenesulfonamide 6a and 3.9 g of N,N′-(2,2′-(methylazanediyl)-bis(ethane-2,1-diyl))bis(2-nitrobenzenesulfonamide) 6b; m/z (6a)=303 (M+H)+, m/z (6b)=488 (M+H)+.

Workup

  1. washthe reaction mixture (RM) was washed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel with a gradient of methanol in DCM (0 to 10%)

Sources & evidence

ORD record
ord-d249da6a85cc4539a9fd345329f849c9
Source dataset
uspto-grants-2014_12
Patent number
US08921355B2

Reaction notes

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