Methanol → HCID 54251925, compound

HRID 1419090Notes

Reaction equation

HRID 1419090 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH2:8][O:9][CH2:10]2)=[CH:5][CH:4]=1.[F:14][C:15]([F:22])([F:21])[C:16](OCC)=O.C[O-].[Na+].CO.[CH:28]1[C:33]([NH:34][NH2:35])=[CH:32][CH:31]=[C:30]([S:36]([NH2:39])(=[O:38])=[O:37])[CH:29]=1.Cl>C(OCC)C.Cl.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:34]([C:33]4[CH:28]=[CH:29][C:30]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:31][CH:32]=4)[N:35]=[C:16]([C:15]([F:14])([F:21])[F:22])[C:8]=3[O:9][CH2:10][C:11]=2[CH:12]=1

Participants

9

Reactant 5

HCID 887MethanolHCID 9794Ethyl trifluoroacetateHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 10942334Sodium MethoxideHCID 145307827-Methoxy-1H-2-benzopyran-4(3H)-one

Product 1

HCID 54251925HCID 54251925, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7-methoxyisochroman-4-one (3.96 g, 22.2 mmol) and ethyl trifluoroacetate (2.90 mL, 5.8 mmol) was dissolved in 30 mL of diethyl ether and treated with a solution of 25% sodium methoxide in methanol (5.8 mL, 26.7 mmol). The solution was stirred at room temperature for 1 hour. The solution was diluted with 1N HCl and extracted with ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford a solid. The crude reaction product was dissolved in 50 mL of ethanol and treated with 4-sulfonamidophenylhydrazine hydrochloride (5.47 g, 24.4 mmol). This solution was heated to reflux for 3.5 hours, cooled to room temperature, diluted with 100 mL of 1N HCl. After cooling the solution to 0° C. for ca. 0.5 hour, crystals of pure 4-[1,5-dihydro-7-methoxy-3-(trifluoromethyl)-[2]benzopyrano[4,3-c]pyrazol-1-yl]benzenesulfonamide formed that were isolated by filtration and dried in vacuo to afford 7.56 g (80%): mp 275° C. (dec). 1H NMR (CDCl3 300 MHz) 7.91 (d, J=8.66 Hz, 2H), 7.54 (d, J=8.66 Hz, 2H), 6.69-6.54 (m, 5H), 5.07 (s, 2H), 3.63 (s, 3H). 19F NMR (CDCl3 282 MHz) -62.01(s). Anal. calc'd. for C18H14F3N3O4S: C, 50.82; H, 3.32; N, 9.88; S, 7.54. Found: C, 50.93; H, 3.38; N, 9.94; S, 7.57.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a solid
  7. customThe crude reaction product
  8. temperatureThis solution was heated
  9. temperatureto reflux for 3.5 hours
  10. temperaturecooled to room temperature
  11. temperatureAfter cooling the solution to 0° C. for ca. 0.5 hour

Sources & evidence

ORD record
ord-a7801fc58ac949a89c033721636f3283
Source dataset
uspto-grants-1999_03
Patent number
US05886016

Reaction notes

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