Propylamine → 2-Nitro-N-propylbenzenesulfonamide

HRID 1487227Notes

Reaction equation

HRID 1487227 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22])([O-:14])=[O:13]>O1CCCC1>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:4][CH2:1][CH2:2][CH3:3])(=[O:23])=[O:22])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 23033002-Nitro-N-propylbenzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of propan-1-amine (2.36 g, 0.04 mol) in tetrahydrofuran (100 mL) at 0° C. was added triethylamine (4.05 g, 0.04 mol) and 2-nitrobenzene-1-sulfonyl chloride (8.88 g, 0.04 mol) in several portions over 10-15 minutes. The reaction mixture was stirred at room temperature for 4 hours, filtered and concentrated to afford the product 2-nitro-N-propylbenzenesulfonamide (9.18 g, yield 93.9%). 1H NMR (400 MHz, CDCl3) δ ppm 8.11-8.16 (m, 1H), 7.84-7.89 (m, 1H), 7.74-7.79 (m, 2H), 5.26 (s, 1H), 3.05-3.10 (t, 2H, J=6.4 Hz), 1.51-1.60 (m, 2H), 0.89-0.92 (t, 3H, J=7.6 Hz).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d57764c5a3114602832e5f8c54345d84
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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