반응 #55088

ord-2c732e86b9fd4049868c8fe72fbf1b83

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타equipped with a magnetic stirrer, a condenser
  2. 2
    온도The mixture is heated
  3. 3
    온도to reflux
  4. 4
    온도boiling is maintained for about 15 minutes
  5. 5
    온도Thereafter the mixture is cooled
  6. 6
    온도The whole is heated
  7. 7
    온도under reflux for about 30 minutes
  8. 8
    온도cooled
  9. 9
    온도Thereafter the whole is heated
  10. 10
    온도under reflux for 30 minutes
  11. 11
    온도cooled
  12. 12
    기타the oil obtained
  13. 13
    세척the solution is washed with a dilute solution of sodium bicarbonate
  14. 14
    여과filtered over charcoal
  15. 15
    기타thus precipitates
  16. 16
    여과is filtered off

실험 절차

A solution of 15.2 g (0.2 mol) of thiourea in 100 ml of water is introduced into a 1 liter 3-necked flask equipped with a magnetic stirrer, a condenser and dropping funnel, and 28.9 g (0.2 mol) of p-fluorobenzylchloride are introduced, at 50°-60° C., in a single operation. The mixture is heated to reflux and boiling is maintained for about 15 minutes; the solution becomes limpid. Thereafter the mixture is cooled and a solution of 32 g (0.8 mol) of NaOH in water is added dropwise at about 60° C. The whole is heated under reflux for about 30 minutes and cooled and a solution of about 0.28 mol of sodium chloroacetate (obtained by neutralising 26.46 g of chloroacetic acid in 200 ml of water with 23.52 g of sodium bicarbonate) is added dropwise at 60°-70° C. Thereafter the whole is heated under reflux for 30 minutes, and then cooled. The mixture is acidified with 3 N HCl, the oil obtained is taken up in methylene chloride, the solution is washed with a dilute solution of sodium bicarbonate, filtered over charcoal and acidified once more with 3 N HCl and p-fluorobenzylthioacetic acid thus precipitates and is filtered off. After recrystallisation from cyclohexane, 33.4 g (yield: 83%) of the said acid are collected. Instantaneous melting point: 68°-69° C.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04151300uspto-grants-1979_04