Sodium Hydroxide → N-(2-bromoethyl)-1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxaline sulfonamide

HRID 1416153Notes

Reaction equation

HRID 1416153 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[OH-].[Na+].[O:8]=[C:9]1[C:18](=[O:19])[NH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([S:20](Cl)(=[O:22])=[O:21])[CH:15]=2)[NH:10]1>O>[Br:2][CH2:3][CH2:4][NH:5][S:20]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:8])[C:18](=[O:19])[NH:17]2)(=[O:21])=[O:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27742172-Bromoethylamine hydrobromideHCID 49837382,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride

Product 1

HCID 53792021N-(2-bromoethyl)-1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxaline sulfonamideYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.49 g (0.1 mole) of 2-bromoethylamine hydrobromide and 4.00 g (0.1 mole) of sodium hydroxide are dissolved in 60 ml of water, and 7.82 g (0.03 mole) of 1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxalinesulfonyl chloride are added to the solution, and the mixture is stirred at room temperature for 6 hours. Then it is allowed to stand for 16 hours. 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 3.44 g (33%) of N-(2-bromoethyl)-1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxaline sulfonamide are obtained, m.p.: 261-266° C.

Workup

  1. waitto stand 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-19847b66b4cd41129897a1fdf91e43f8
Source dataset
uspto-grants-1999_06
Patent number
US05912245

Reaction notes

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