Acetic Acid → HCID 54442755, compound

HRID 1416159Notes

Reaction equation

HRID 1416159 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([NH:8][C:9](=[O:15])[C:10](=[O:14])[NH:11]2)=[CH:6][C:5]=1[S:16](Cl)(=[O:18])=[O:17])([O-:3])=[O:2].[CH3:20][NH:21][CH3:22].C(O)(=O)C>O>[CH3:20][N:21]([CH3:22])[S:16]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:4]=1[N+:1]([O-:3])=[O:2])[NH:11][C:10](=[O:14])[C:9](=[O:15])[NH:8]2)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 674DimethylamineHCID 54433101HCID 54433101, compound

Product 1

HCID 54442755HCID 54442755, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.58 g (0.015 mole) of 1,2,3,4-tetrahydro-7-nitro-2,3-dioxo-6-quinoxalinesulfonyl chloride and 30 ml of 25% ethanolic dimethylamine is stirred at a temperature between 5° C. and 10° C. for 3 hours, and then allowed to stand for 16 hours. To the reaction mixture 5 ml of acetic acid and 60 ml of water are added, the separated crystals are filtered, washed with water and acetone, dried, dissolved in a slight amount of hot dimethyl sulfoxide and precipitated from this solution with water. Thus 3.80 g (81%) of N,N-dimethyl-1,2,3,4-tetrahydro-7-nitro-2,3-dioxo-6-quinoxaline sulfonamide are obtained, m.p.: 318-332° C.

Workup

  1. waitto stand for 16 hours
  2. filtrationthe separated crystals are filtered
  3. washwashed with water and acetone
  4. customdried
  5. dissolutiondissolved in a slight amount of hot dimethyl sulfoxide
  6. customprecipitated from this solution with water

Sources & evidence

ORD record
ord-399722e7969b4c22b78de0325090173f
Source dataset
uspto-grants-1999_06
Patent number
US05912245

Reaction notes

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