p-Toluenesulfonic acid → HCID 86601656, compound

HRID 1865809Notes

Reaction equation

HRID 1865809 reaction equation
[Cl:1][C:2]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9]O)=[O:5].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.C1(C)C=CC(S(O)(=O)=[O:34])=CC=1>C(Cl)Cl>[Cl:1][C:2]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH:8]([O:34][CH:26]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[CH3:9])=[O:5]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 86048451HCID 86048451, compound

Product 1

HCID 86601656HCID 86601656, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 13 (1.22 g, 4.0 mmol) in 50 mL of CH2Cl2 was cooled in an ice-bath, and 3,4-dihydro-2H-pyran (1.0 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)propyl]benzamide (21) (1.45 g, 94%): as a pale yellow oil; 1H NMR [(CD3)2SO] δ 8.99 (d, J=2.7 Hz, 1 H, H-4), 8.81 (m, 1 H, CONH), 8.51 (d, J=2.7 Hz, 1 H, H-6), 4.57 (m, 1 H), 3.72 (m, 2 H), 3.46-3.25 (m, 4 H), 1.82-1.44 (m, 8 H). 13C NMR δ 162.7, 148.4, 145.9, 140.3, 128.2, 125.8, 120.5, 98.0, 64.2, 61.3, 36.5, 30.2, 28.9, 24.9, 19.1. HRMS (FAB) Calcd. For C15H1935ClIN3O7 [M+H+] m/z 388.0912. Found; 388.0915.

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-1ee5a896a8bb41ebb43eac747d12462c
Source dataset
uspto-grants-2009_12
Patent number
US07629332B2

Reaction notes

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