p-Toluenesulfonic acid → 2-nitro-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamide

HRID 1183079Notes

Reaction equation

HRID 1183079 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].[NH2:14][CH2:15][CH2:16][CH2:17][OH:18].C(N(CC)CC)C.[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>ClCCl.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:14][CH2:15][CH2:16][CH2:17][O:18][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][O:26]1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

9

Reactant 6

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 14798Sodium HydroxideHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 686733412-nitro-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamideYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

2-Nitrobenzenesulfonyl chloride (22.1 g, 0.10 mol) was added to a dichloromethane solution (400 ml) of 3-aminopropanol (8.2 g, 0.11 mol) and triethylamine (21 ml, 0.15 mol) at 0° C., and stirred at room temperature overnight. Water was added to the reaction mixture and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in dichloromethane (400 ml), and 3,4-dihydro-2H-pyrane (9.3 g, 0.11 mol) and p-toluenesulfonic acid (1.9 g, 0.01 mol) were added thereto. Stirring was conducted at room temperature overnight. A 1N-sodium hydroxide aqueous solution was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:2). The purified product was concentrated under reduced pressure to thereby obtain 27.56 g (yield: 80%) of 2-nitro-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamide as a pale brown oil.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (400 ml)
  4. stirringStirring
  5. waitwas conducted at room temperature overnight
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:2)
  10. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c95704bc48e74dc9992fefbdb766b7bd
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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