Sulfuric Acid → HCID 15461581, compound

HRID 1385202Notes

Reaction equation

HRID 1385202 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20].S(=O)(=O)(O)O.CCOCC>O1CCOCC1>[O:14]=[C:3]1[C:2]2[N:1]=[C:19]([C:18]3[CH:22]=[CH:23][CH:24]=[C:16]([CH3:15])[CH:17]=3)[O:20][C:11]=2[C:10](=[O:13])[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 177482-Amino-3-chloro-1,4-naphthoquinoneHCID 743753-Methylbenzoyl chloride

Product 1

HCID 15461581HCID 15461581, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5 g (24 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxo-naphthalene in 70 mL of dioxane, one adds, with protection from light, 32.00 mL (240 mmol) of 3-methylbenzoic acid chloride; after 5 min of stirring, 0.50 mL of concentrated sulfuric acid is added. After 45 min of reflux and complete cooling, 200 mL of ether are added, and the precipitate that forms is eliminated by filtration. The red filtrate is evaporated to dryness, redissolved in dichloromethane, washed several times with water, dried and purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 50/50). The yellow crystals formed after evaporation of the solvent are uncolored and recrystallized in dichloromethane to produce 3 g of 4,9-dihydro-4,9-dioxo-2-(3-methylphenyl)-naphtho[2,3-d]oxazole in the form of yellow crystals.

Workup

  1. temperatureAfter 45 min of reflux
  2. filtrationthe precipitate that forms is eliminated by filtration
  3. customThe red filtrate is evaporated to dryness
  4. dissolutionredissolved in dichloromethane
  5. washwashed several times with water
  6. customdried
  7. custompurified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 50/50)
  8. customThe yellow crystals formed
  9. customafter evaporation of the solvent
  10. customrecrystallized in dichloromethane

Sources & evidence

ORD record
ord-d408898ebdae40eb8232795958342947
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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