p-Toluenesulfonic acid → HCID 22097183, compound

HRID 1458829Notes

Reaction equation

HRID 1458829 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]([CH2:15][CH3:16])[C:7](=[O:17])[C:6](=[O:18])[NH:5]2.CO[CH:21]1[CH2:25][CH2:24][CH:23](OC)O1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:15]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([N:1]3[CH:21]=[CH:25][CH:24]=[CH:23]3)=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][C:6](=[O:18])[C:7]1=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 22097137HCID 22097137, compound

Product 1

HCID 22097183HCID 22097183, compoundYield 374.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

4.0 g (16 mmol) of 6-amino-1-ethyl-7-nitro-2,3(1H,4H)-quinoxalinedione, 2.4 g (18 mmol) of 2,5-dimethoxytetrahydrofuran and a spatula tip of p-toluenesulfonic acid were refluxed in a mixture of 50 ml of dimethylformamide and 50 ml of toluene with a water trap for 3 h. The mixture was then concentrated under reduced pressure, and the residue was treated with methanol. The precipitate was filtered off with suction to yield 18 g (3%) of the product.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionthe residue was treated with methanol
  3. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-1fae06081d2a4204a10f9cd62de9c794
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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