Acetic Acid → HCID 15345817, compound

HRID 1385206Notes

Reaction equation

HRID 1385206 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-2:15].[Na+].[Na+].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.C(O)(=O)C>O>[O:14]=[C:3]1[C:2]2[N:1]=[C:21]([C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[F:18])[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 14804Sodium SulfideHCID 177482-Amino-3-chloro-1,4-naphthoquinoneHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 15345817HCID 15345817, compoundYield 27%

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 80 mL of water, 8.4 g (35 mmol) of nonahydrated sodium sulfide are added. The reaction mixture is then heated to reflux for approximately 20 min, then 20 mL of an aqueous solution containing 2.0 g of sodium sulfide are added. When the color of the medium has completely changed to blue, 1.95 mL (24 mmol) of 2-fluorobenzaldehyde and 6.36 mL of glacial acetic acid are added successively. After 1 h of reflux, the black semisolid product obtained is filtered, dried, and purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 50/50). The greenish crystals formed after evaporation of the solvent are washed several times with ethanol and ether, then they are uncolored and recrystallized in dichloromethane to produce 2.0 g of 4,9-dihydro-4,9-dioxo-2-(2-fluorophenyl)-naphtho[2,3-d]thiazole in the form of yellow crystals.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is then heated
  3. temperatureto reflux for approximately 20 min
  4. additionare added
  5. additionare added successively
  6. temperatureAfter 1 h of reflux
  7. customthe black semisolid product obtained
  8. filtrationis filtered
  9. customdried
  10. custompurified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 50/50)
  11. customThe greenish crystals formed
  12. customafter evaporation of the solvent
  13. washare washed several times with ethanol and ether
  14. customrecrystallized in dichloromethane

Sources & evidence

ORD record
ord-57d5bb3c73824199a425c89e1f19e300
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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