p-Toluenesulfonic acid → 1-Cyclohexyl-6-(2-methoxycarbonyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedione

HRID 861489Notes

Reaction equation

HRID 861489 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]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7](=[O:21])[C:6](=[O:22])[NH:5]2.[CH3:23][O:24][C:25]([C:27]1(OC)[CH2:31][CH2:30][CH:29](OC)O1)=[O:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH:15]1([N:8]2[C:9]3[C:4](=[CH:3][C:2]([N:1]4[CH:29]=[CH:30][CH:31]=[C:27]4[C:25]([O:24][CH3:23])=[O:26])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=3)[NH:5][C:6](=[O:22])[C:7]2=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 13152840Methyl 2,5-dimethoxyoxolane-2-carboxylateHCID 220970786-Amino-1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 220971601-Cyclohexyl-6-(2-methoxycarbonyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedioneYield 80.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

10 g (33 mmol) of 6-amino-1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedione (Example 28e), 6.9 g (36 mmol) of 2-methoxycarbonyl-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. After reaction was complete, the mixture was concentrated under reduced pressure, and the residue was treated with water. The precipitate was filtered off with suction to yield 11 g (79%) of the product. Melting point 211°-212° C.

Workup

  1. customAfter reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionthe residue was treated with water
  4. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-a76a64408e5b4558ac97d49e6a2cf814
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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