p-Toluenesulfonic acid → HCID 24755819, compound

HRID 503677Notes

Reaction equation

HRID 503677 reaction equation
[Cl:1][C:2]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][OH:9])=[O:5].[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Cl:1][C:2]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][O:9][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:20]1)=[O:5]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 59325909HCID 59325909, compound

Product 1

HCID 24755819HCID 24755819, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 12b (0.6 g, 2.14 mmol) in CH2Cl2 was cooled in an ice-bath, and 3,4-dihydro-2H-pyran (2.0 mL) and p-toluenesulfonic acid (0.1 g) were added. The reaction mixture was stirred for 2 h, then concentrated under reduced pressure. Chromatography of the residue on silica gel, eluting with EtOAc/petroleum ether (from 1:2 to 2:1), gave 2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (12c) (0.8 g, 100%): as an oil;

Workup

  1. concentrationconcentrated under reduced pressure
  2. washChromatography of the residue on silica gel, eluting with EtOAc/petroleum ether (from 1:2 to 2:1)

Sources & evidence

ORD record
ord-37db0b0da87a4feea28b9ee4d6e1cc7f
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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