Hydrochloric Acid → (3,5-Difluorophenyl)thiourea

HRID 907708

Reaktionsgleichung

Reaktionsgleichung von HRID 907708
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[F:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([F:22])[CH:21]=1)[NH2:18].[OH-].[Na+].Cl.[OH-].[NH4+]>CC(C)=O.O>[F:14][C:15]1[CH:16]=[C:17]([NH:18][C:11]([NH2:12])=[S:10])[CH:19]=[C:20]([F:22])[CH:21]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 15666Ammonium thiocyanateHCID 965953,5-Difluoroaniline

Produkt 1

HCID 2783293(3,5-Difluorophenyl)thioureaAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Benzoyl chloride (5.44 g, 38.73 mmol) was added to a stirred solution of ammonium thiocyanate (3.83 g, 50.35 mmol) in acetone (80 mL) at 30° C. The mixture was stirred at reflux for 30 minutes, then cooled to 50° C., and a solution of 3,5-difluoroaniline (5.00 g, 38.73 mmol) in acetone (10 mL) was added in one portion. The mixture was stirred at reflux for 30 minutes. A solution of NaOH (5.42 g, 135.54 mmol) in water (65 mL) was added, and the mixture was stirred at reflux for 20 minutes and then cooled to 20° C. Concentrated HCl was added to adjust the acidity to pH=5, and then the mixture was adjusted to slightly alkaline by the addition of conc. ammonium hydroxide. After 30 minutes, the mixture was cooled to 10° C. and extracted with EtOAc, and the combined organic layer was washed with brine, filtered, and concentrated to afford N-(3,5-difluorophenyl)thiourea (3.52 g, 48%). ret. time 1.73; m/z 189.0 (MH+); 1H NMR (400 MHz, MeOH-d4) δ 6.72 (m, 1H), 7.16 (m, 2H).

Aufarbeitung

  1. temperatureat reflux for 30 minutes
  2. stirringThe mixture was stirred
  3. temperatureat reflux for 30 minutes
  4. stirringthe mixture was stirred
  5. temperatureat reflux for 20 minutes
  6. temperaturecooled to 20° C
  7. temperaturethe mixture was cooled to 10° C.
  8. extractionextracted with EtOAc
  9. washthe combined organic layer was washed with brine
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-42fda4856e4841e09d0b00536e045ff3
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013166B2

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