Chlorosulfonic acid → 1,4-Dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride

HRID 658655Notes

Reaction equation

HRID 658655 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[C:9](=[O:18])[C:8]1=[O:19]>>[CH3:17][N:10]1[C:11]2[C:16](=[CH:15][C:14]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:13][CH:12]=2)[N:7]([CH3:6])[C:8](=[O:19])[C:9]1=[O:18]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 3514211,4-Dimethylquinoxaline-2,3-dione

Product 1

HCID 463183331,4-Dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride

Procedure

Chlorosulfonic acid (3 mL) was heated to 65° C. and 1,4-dimethylquinoxaline-2,3(1H,4H)-dione (example 6-3b, 1 g, 5.5 mmol) was added in portions over 0.5 hour. The reaction mixture was stirred for 4 hours then cooled to ambient temperature and poured slowly onto ice. The resulting precipitate was filtered and washed with water to give 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride as a white solid. 1H NMR (400 MHz, DMSO-d6): δ, ppm: 3.50 (s, 6H), 7.25 (m, 2H), 7.38 (m, 4H).

Workup

  1. additionpoured slowly onto ice
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-e951cf62e65844b289b8a33d39094e59
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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