Acetic Acid → HCID 15461585, compound

HRID 1385207Notes

Reaction equation

HRID 1385207 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.[S:15]([O-])([O-])(=O)=O.[Na+].[Na+].[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C(O)(=O)C>O>[O:14]=[C:3]1[C:2]2[N:1]=[C:27]([C:26]3[CH:29]=[CH:30][C:23]([F:22])=[CH:24][CH:25]=3)[S:15][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 176Acetic AcidHCID 177482-Amino-3-chloro-1,4-naphthoquinoneHCID 24436Sodium SulfateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 15461585HCID 15461585, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 5.0 g (24 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene in 130 mL of water, 8.4 g (35 mmol) of nonahydrated sodium sulfide are added. The reaction mixture is heated to reflux for 20 min, then 50 mL of an aqueous solution containing 1.0 g of sodium sulfate are added. The color of the medium changes completely to blue. 2.60 mL (24 mmol) of 4-fluorobenzaldehyde and 6.36 mL of glacial acetic acid are added successively. After 1 h of reflux, the greenish precipitate obtained is filtered, dried, and purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 60/40). The yellow crystals formed after evaporation of the solvent are washed successively with the isopropanol and ether, then uncolored and recrystallized in dichloromethane to produce 2.0 g of 4,9-dihydro-4,9-dioxo-2-(4-fluorophenyl)naphtho[2,3-d]thiazole in the form of yellow crystals.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 20 min
  4. additionare added
  5. temperatureAfter 1 h of reflux
  6. customthe greenish precipitate obtained
  7. filtrationis filtered
  8. customdried
  9. custompurified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 60/40)
  10. customThe yellow crystals formed
  11. customafter evaporation of the solvent
  12. washare washed successively with the isopropanol and ether
  13. customuncolored and recrystallized in dichloromethane

Sources & evidence

ORD record
ord-c8117757c8d042869113d00587ba33e2
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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