Hydrochloric Acid → (3,5-Difluorophenyl)thiourea

HRID 9569

반응식

HRID 9569 반응식
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

참가 물질

9

반응물 6

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

생성물 1

HCID 2783293(3,5-Difluorophenyl)thiourea수율 48.3%

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0c0dac246ef34adebe28927fa5547233
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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