반응 #9665

반응 방정식

ammonium hydroxide

NaOH

Benzoyl chloride

ammonium thiocyanate

3,5-difluoroaniline

HCl

→

N-(3,5-difluorophenyl) thiourea

수율 48.3%

용매

water

acetone

acetone

반응 조건

후처리

1. 1
   온도at reflux for 30 minutes
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   온도at reflux for 30 minutes
4. 4
   workup.STIRRINGthe mixture was stirred
5. 5
   온도at reflux for 20 minutes
6. 6
   온도cooled to 20° C
7. 7
   온도the mixture was cooled to 10° C.
8. 8
   추출extracted with EtOAc
9. 9
   세척the combined organic layer was washed with brine
10. 10
    여과filtered
11. 11
    농축concentrated

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).

출처