tert-Butyl mercaptan → Methyl 3-[(tert-butylthio)diazenyl]-4-fluoro-2-methylbenzoate

HRID 1639803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639803
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6].[N:14]([O-])=O.[Na+].C([O-])(=O)C.[K+].[CH3:23][C:24]([SH:27])([CH3:26])[CH3:25]>Cl.O.C(O)C>[C:24]([S:27][N:14]=[N:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6])([CH3:26])([CH3:25])[CH3:23]

Komponenten

8

Edukt 4

HCID 6387tert-Butyl mercaptanHCID 517044Potassium AcetateHCID 23668193Sodium NitriteHCID 59334547Methyl 3-amino-4-fluoro-2-methylbenzoate

Produkt 1

HCID 86641924Methyl 3-[(tert-butylthio)diazenyl]-4-fluoro-2-methylbenzoateAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-amino-4-fluoro-2-methylbenzoate (3.00 g, 16.4 mmol) in hydrochloric acid (6 N, 54.6 mL) was added a solution of sodium nitrite (1.24 g, 18.0 mmol) in water (3 mL) at 0° C., and the mixture was stirred for 2 hr. To the reaction solution was added aqueous potassium acetate solution (30%) at 0° C. to adjust the reaction solution to pH 4, and a solution of 2-methylpropane-2-thiol (2.03 mL, 18.0 mmol) in ethanol (3 mL) was added. The reaction solution was stirred at room temperature for 12 hr, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give methyl 3-[(tert-butylthio)diazenyl]-4-fluoro-2-methylbenzoate (2.90 g, yield 62%) as a crudely purified product.

Aufarbeitung

  1. stirringThe reaction solution was stirred at room temperature for 12 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-75e798ba64614d9f80a6f1a8517a7086
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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