Propylamine → (3-nitrophenyl)-N-propylmethanesulfonamide

HRID 1890979Notes

Reaction equation

HRID 1890979 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][S:11](Cl)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:15]([NH2:18])[CH2:16][CH3:17].C(N(CC)CC)C>C(#N)C.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][S:11]([NH:18][CH2:15][CH2:16][CH3:17])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 13196775(3-Nitrophenyl)methanesulfonyl chloride

Product 1

HCID 28636111(3-nitrophenyl)-N-propylmethanesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(3-Nitrophenyl)methanesulfonyl chloride (0.6 g, 2.55 mmol) was dissolved in acetonitrile (10 mL), then to this solution was added propylamine (0.247 ml, 3 mmol) and triethylamine (1 mL) and the reaction mixture was vigorously stirred for 3 h at room temperature. The obtained mixture was diluted with cold water (30 ml), which led to the formation of a precipitate that was filtered off, washed with water (2×10 mL) and dried. Yield of (3-nitrophenyl)-N-propylmethanesulfonamide 0.63 g (95%).

Workup

  1. filtrationwas filtered off
  2. washwashed with water (2×10 mL)
  3. customdried

Sources & evidence

ORD record
ord-4de78143ccae43e6aef39c493425dd13
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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