Sulfuric Acid → HCID 21184353, compound

HRID 1385197Notes

Reaction equation

HRID 1385197 reaction equation
[O:1]=[C:2]1[C:14]2[N:13]=[C:12]([CH3:15])[N:11]([CH3:16])[C:10]=2[C:9](=[O:17])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[S:18](=[O:22])(=[O:21])([OH:20])[OH:19]>CO.ClCCl>[S:18]([OH:22])([OH:21])(=[O:20])=[O:19].[O:1]=[C:2]1[C:14]2[N:13]=[C:12]([CH3:15])[N:11]([CH3:16])[C:10]=2[C:9](=[O:17])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 2849251h-naphth[2,3-d]imidazole-4,9-dione, 1,2-dimethyl-

Product 1

HCID 21184353HCID 21184353, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2 g (8.84 mmol) of 4,9-dihydro-4,9-dioxo-1,2-dimethyl-1H-naphtho[2,3-d]imidazole in 300 mL of a methanol/dichloromethane mixture (2/1) heated at 70° C., 1 mL of concentrated sulfuric acid is added. The reaction mixture is stirred at 70° C. for 2 h, then concentrated at reduced pressure, and the pale yellow precipitate that appears is filtered and washed with dichloromethane, then with ethyl ether, to produce 2 g of 4,9-dihydro-4,9-dioxo-1,2-dimethyl-1H-naphtho[2,3-d]imidazole sulfate, in the form of yellow crystals.

Workup

  1. concentrationconcentrated at reduced pressure
  2. filtrationthe pale yellow precipitate that appears is filtered
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-ea32dea9caae40d99428d22d796d2f45
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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