Acetic Acid → 2,3-dihydroxy-N-(2-methoxyethyl)quinoxaline-6-sulfonamide

HRID 1416157Notes

Reaction equation

HRID 1416157 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[O:6]=[C:7]1[C:16](=[O:17])[NH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([S:18](Cl)(=[O:20])=[O:19])[CH:13]=2)[NH:8]1.C(O)(=O)C>O>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:18]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:6])[C:16](=[O:17])[NH:15]2)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 49837382,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride

Product 1

HCID 175983032,3-dihydroxy-N-(2-methoxyethyl)quinoxaline-6-sulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 7.51 g (0.1 mole) of 2-methoxyethylamine in 20 ml of water 5.21 g (0.02 mole) of 1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxalinesulfonyl chloride are added in small portions, under stirring, and the mixture is stirred at room temperature for 16 hours. It is allowed to stand further for 2 days, and then 15 ml of acetic acid and 10 ml of water are added to it. The separated crystals are filtered, washed successively with water and acetone, dried, dissolved in a slight amount of hot dimethyl sulfoxide and precipitated from the solution with water. Thus 3.80 g (63%) of 1,2,3,4-tetra-hydro-N-(2-methoxy-ethyl)-2,3-dioxo-6-quinoxaline sulfonamide are obtained, m.p.: 264-267° C.

Workup

  1. stirringthe mixture is stirred at room temperature for 16 hours
  2. filtrationThe separated crystals are filtered
  3. washwashed successively with water and acetone
  4. customdried
  5. dissolutiondissolved in a slight amount of hot dimethyl sulfoxide
  6. customprecipitated from the solution with water

Sources & evidence

ORD record
ord-1146d7e83d974b508a18bc1f3798dcc3
Source dataset
uspto-grants-1999_06
Patent number
US05912245

Reaction notes

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