Sulfuric Acid → HCID 15461582, compound

HRID 1385205Notes

Reaction equation

HRID 1385205 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.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.S(=O)(=O)(O)O>O1CCOCC1>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]2[O:21][C:11]3[C:10](=[O:13])[C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[C:3](=[O:14])[C:2]=3[N:1]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 85014-Chlorobenzoyl chlorideHCID 177482-Amino-3-chloro-1,4-naphthoquinone

Product 1

HCID 15461582HCID 15461582, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5.0 g (24 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene in 60 mL of dioxane, one adds at ambient temperature 15.3 mL (120 mmol) of 4-chlorobenzoic acid chloride and 0.5 mL of concentrated sulfuric acid. The reaction mixture is heated to reflux for 4 h, then evaporated to dryness, redissolved in 200 mL of dichloromethane, and neutralized at cold temperature with 100 mL of 10N sodium hydroxide. The organic phase is then washed three times with water and dried over calcium chloride. The red powder so obtained is purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 70/30). The yellow crystals obtained after evaporation of the solvent are uncolored and recrystallized in dichloromethane to produce 2.5 g of 2-(4-chlorophenyl)-4,9-dihydro-4,9-dioxo-naphtho[2,3-d]oxazole in the form of yellow crystals.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 4 h
  3. customevaporated to dryness
  4. dissolutionredissolved in 200 mL of dichloromethane
  5. washThe organic phase is then washed three times with water
  6. dry with materialdried over calcium chloride
  7. customThe red powder so obtained
  8. customis purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 70/30)
  9. customThe yellow crystals obtained
  10. customafter evaporation of the solvent
  11. customrecrystallized in dichloromethane

Sources & evidence

ORD record
ord-9002f73a12a640d3a859981aae2a7be1
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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