Dichloromethane → 2-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamide

HRID 68998

Reaction equation

HRID 68998 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].ClCCl.[NH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C>O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:17][CH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 8540512-(Pyridin-3-yl)ethan-1-amine

Product 1

HCID 465565342-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamideYield 32.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Nitrobenzene sulfonyl chloride (11.64 g) was added to a dichloromethane solution (100 ml) of 3-(2-aminoethyl)pyridine (6.11 g) and triethylamine (9 ml) at 0° C. The mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound (5.06 g) as a yellow powder.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure
  3. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c3ccd1da4a8f4ca2bfbf69713a3fb167
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Linked notes

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