Hydrochloric Acid → HCID 178526175、化合物

HRID 26810

反応式

HRID 26810 の反応式
NC(N)=[S:3].[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Cl)=[CH:8][CH:7]=1.[OH-].[Na+].Cl[CH2:17][C:18]([O-:20])=O.[Na+].Cl>O.C(Cl)Cl.C1CCCCC1>[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][CH2:17][C:18]([OH:20])=[S:3])=[CH:8][CH:7]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 96024-Fluorobenzyl chlorideHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 23665759Sodium chloroacetate

生成物 1

HCID 178526175HCID 178526175、化合物収率 90.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 8078Cyclohexane溶媒

実験手順

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.

後処理

  1. customequipped with a magnetic stirrer, a condenser
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. temperatureboiling is maintained for about 15 minutes
  5. temperatureThereafter the mixture is cooled
  6. temperatureThe whole is heated
  7. temperatureunder reflux for about 30 minutes
  8. temperaturecooled
  9. temperatureThereafter the whole is heated
  10. temperatureunder reflux for 30 minutes
  11. temperaturecooled
  12. customthe oil obtained
  13. washthe solution is washed with a dilute solution of sodium bicarbonate
  14. filtrationfiltered over charcoal
  15. customthus precipitates
  16. filtrationis filtered off

出典と根拠

ORDレコード
ord-2c732e86b9fd4049868c8fe72fbf1b83
出典データセット
uspto-grants-1979_04
特許番号
US04151300

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