3-Nitrobenzenesulfonyl chloride → HCID 17639086, compound

HRID 914959Notes

Reaction equation

HRID 914959 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18]>C(Cl)Cl.CCOC(C)=O>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:18][S:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 17639086HCID 17639086, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitrobenzenesulfonyl chloride (1, 1.0 g, 4.51 mmol) in anhydrous CH2Cl2 (9.0 mL) was added N,N-dimethyl-ethylenediamine (2, 0.5 mL, 4.55 mmol) dropwise. The resulting solution was stirred at room temperature overnight before it was diluted with EtOAc (80 mL). The organic mixture was washed with saturated NaHCO3 (90 mL), brine (90 mL), and dried over MgSO4. The solids were filtered and the filtrate was concentrated on a rotavap to give 3 as a foam (0.8 g) which was used in the next step without further purification.

Workup

  1. washThe organic mixture was washed with saturated NaHCO3 (90 mL), brine (90 mL)
  2. dry with materialdried over MgSO4
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate was concentrated on a rotavap

Sources & evidence

ORD record
ord-750bc0c07ad547169594e0c3d1061d3e
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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