2-Nitrobenzenesulfonyl chloride → 1-[(2-nitrophenyl)sulfonyl]pyrrolidine

HRID 1373082Notes

Reaction equation

HRID 1373082 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].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 7473941-[(2-nitrophenyl)sulfonyl]pyrrolidineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Nitrobenzenesulfonyl chloride (4.43 g, 20 mmol) in methylene chloride (20 mL) was added dropwise to the ice-cooled solution of pyrrolidine (8.4 mL, 100 mmol) in methylene chloride (100 mL). The reaction mixture was stirred at room temperature for 2 hours and washed with 3N HCl (2×60 mL) and brine (60 mL). The organic layer was dried (Na2SO4) and concentrated to yield the intermediate nitrobenzene derivative (5.12 g, 100%). 1H NMR (400 MHz, CDCl3) δ: 8.00 (d, 1H), 7.70 (m, 2H), 7.60 (d, 1H), 3.40 (t, 4H), 1.92 (t, 4H), 1.80 (t, 4H).

Workup

  1. washwashed with 3N HCl (2×60 mL) and brine (60 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4d288c424dbe4347b6a7acbeae551761
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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