Hydrochloric Acid → HCID 178526175, compound

HRID 2052404Notes

Reaction equation

HRID 2052404 reaction equation
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

Participants

9

Reactant 5

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

Product 1

HCID 178526175HCID 178526175, compoundYield 90.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

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 refux 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.

Workup

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

Sources & evidence

ORD record
ord-a374b5fdda4e4ef799b53d43b79a90f5
Source dataset
uspto-grants-1980_01
Patent number
US04183951

Reaction notes

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