3,4-dihydro-2H-pyran → HCID 19841414, compound

HRID 1638712Notes

Reaction equation

HRID 1638712 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:18][CH2:19]O)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)(=[O:7])=[O:6].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[CH2:19][CH2:18][N:4]([CH2:3][CH2:2][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 14622573HCID 14622573, compound

Product 1

HCID 19841414HCID 19841414, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N,N-di(2-hydroxyethyl)-4-chloro-3-nitrobenzenesulfonamide (7.1 g, 21.9 mmol), 3,4-dihydro-2H-pyran (4.4 mL, 48 mmol) and p-toluenesulfonic acid hydrate (0.10 g) in methylene chloride (200 mL) was stirred at 20°-25° for 3 days. After washing with a saturated solution of sodium bicarbonate the organic layer was dried (Na2SO4), filtered and concentrated. Flash chromatography of the residue over silica gel with chloroform gave 9.0 g of product.

Workup

  1. washAfter washing with a saturated solution of sodium bicarbonate the organic layer
  2. dry with materialwas dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b281e330de5475ab0ff63176c42ad6c
Source dataset
uspto-grants-1989_11
Patent number
US04880821

Reaction notes

Loading…