2-Aminoresorcinol ditosylate → 2-(3,5-Dimethyl-1H-pyrazol-1-yl)-3-hydroxyphenyl 4-methylbenzenesulfonate

HRID 337343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337343
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]S(C3C=CC(C)=CC=3)(=O)=O)[C:13]=2[NH2:29])(=[O:10])=[O:9])=[CH:4][CH:3]=1>N([O-])=O.[Na+].O.Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]=2[N:29]2[C:17]([CH3:16])=[CH:12][C:13]([CH3:14])=[N:29]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

5

Edukt 1

HCID 867032532-Aminoresorcinol ditosylate

Produkt 1

HCID 867032542-(3,5-Dimethyl-1H-pyrazol-1-yl)-3-hydroxyphenyl 4-methylbenzenesulfonateAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittelHCID 23668193Sodium NitriteLösungsmittel

Versuchsvorschrift

To 278 mg of 2-amino-1,3-phenylene bis(4-methylbenzene sulfonate) was added 0.64 ml of 5N-hydrochloric acid, and to the mixture a solution in which 58 mg of sodium nitrite was dissolved in 0.4 ml of water was added dropwise at 0° C., and stirred for 30 minutes. Then, a solution in which 289 mg of stannous chloride was dissolved in 0.32 ml of 5N-hydrochloric acid was added dropwise at 0° C. and stirred for 1 hour. The solvent was distilled off under reduced pressure, and 1.3 ml of ethanol and 66 μl of acetyl acetone were added and heated at reflux for 2 hours. To the reaction mixture was added 50 ml of water, and neutralized with a saturated sodium bicarbonate solution and extracted with 50 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1) to yield 62.9 mg of the title compound.

Aufarbeitung

  1. additionwas added dropwise at 0° C.
  2. additionwas added dropwise at 0° C.
  3. stirringstirred for 1 hour
  4. distillationThe solvent was distilled off under reduced pressure, and 1.3 ml of ethanol and 66 μl of acetyl acetone
  5. additionwere added
  6. temperatureheated
  7. temperatureat reflux for 2 hours
  8. additionTo the reaction mixture was added 50 ml of water
  9. extractionextracted with 50 ml of ethyl acetate
  10. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-c76a3cc9afb64337ba027a8af58cd767
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889727B2

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