Acetic Acid → HCID 22021863, compound

HRID 1793408Notes

Reaction equation

HRID 1793408 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[S:10][CH2:9][CH:8]([C:12]([O:14]C)=O)[C:7]2=O.[NH:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[NH2:18].C(O)(=O)C>C(OCC)(=O)C>[F:1][C:2]1[C:11]2[S:10][CH:9]=[C:8]3[C:12](=[O:14])[N:17]([C:19]4[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=4)[N:18]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 120894-Hydrazinobenzoic acidHCID 22021867HCID 22021867, compound

Product 1

HCID 22021863HCID 22021863, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 8-fluoro-4-oxothiochromane-3-carboxylate (1.19 g, 4.95 mmol) and 4-hydrazinobenzoic acid (755 mg, 4.95 mmol) were mixed with glacial acetic acid (10 ml). The mixture was heated to reflux for 4 h. Excess acetic acid was removed under vacuum to give an orange oil. Ethyl acetate (10 ml) was added and the mixture sonicated. Precipitation of an orange solid was observed. The solids were collected by filtration and washed with ethyl acetate. The filter cake was taken up in dimethyl suphoxide (10 ml) and air-oxidised at room temperature for one week. Water (20 ml) was added to the reaction mixture, the solids were collected by filtration, slurried in ethyl acetate, filtered and dried under vacuum. The title compound was isolated as an orange powder (175 mg, 0.51 mmol, 10%). LCMS: m/z 341.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. customExcess acetic acid was removed under vacuum
  4. customto give an orange oil
  5. customthe mixture sonicated
  6. customPrecipitation of an orange solid
  7. filtrationThe solids were collected by filtration
  8. washwashed with ethyl acetate
  9. waitair-oxidised at room temperature for one week
  10. additionWater (20 ml) was added to the reaction mixture
  11. filtrationthe solids were collected by filtration
  12. filtrationfiltered
  13. customdried under vacuum

Sources & evidence

ORD record
ord-849c69306ec241d49b259195912ecea5
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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