Hydrochloric Acid → HCID 178526175, compound

HRID 1707020Notes

Reaction equation

HRID 1707020 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 reflux and boiling is maintained for about 15 minutes; the solution becomes limpid. Thereafter the mixtuure 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 chloracetic 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 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. temperatureto reflux
  4. temperatureboiling is maintained for about 15 minutes
  5. temperatureThereafter the mixtuure 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

Sources & evidence

ORD record
ord-b263e15d15c94471b1c6f68aada33963
Source dataset
uspto-grants-1980_06
Patent number
US04209523

Reaction notes

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