2,4-Dichlorobenzyl chloride → 2,4-Dichlorobenzylthio-acetic acid

HRID 26812

Reaction equation

HRID 26812 reaction equation
NC(N)=[S:3].[Cl:5][C:6]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:7]=1[CH2:8]Cl.[OH-].[Na+].Cl[CH2:18][C:19]([O-:21])=O.[Na+]>O>[Cl:5][C:6]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:7]=1[CH2:8][CH2:18][C:19]([OH:21])=[S:3]

Participants

6

Reactant 4

HCID 72122,4-Dichlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 23665759Sodium chloroacetate

Product 1

HCID 1785261732,4-Dichlorobenzylthio-acetic acidYield 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

15.2 g (0.2 mol) of thiourea in 100 ml of water are introduced into a 1 liter 3-necked flask. The mixture is heated to 50°-60° C. and 39.1 g (0.2 mol) of 2,4-dichlorobenzylchloride are introduced in a single operation. The mixture is heated under reflux and boiling is maintained for 15 minutes; the solution becomes limpid. The mixture is cooled and a solution of 32 g (0.8 mol) of NaOH in 50 ml of water is introduced dropwise at about 60° C. The mixture is again heated under reflux for 30 minutes, 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 NaHCO3) is introduced, dropwise, at 60°-70° C. The whole is then heated under reflux for 30 minutes, cooled, filtered and acidified with 3 N HCl; the precipitate obtained is filtered off and redissolved cold in dilute sodium bicarbonate solution, and this solution is washed with methylene chloride, filtered and again acidified. 41.7 g (yield: 83 %) of product are thus collected. Instantaneous melting point: 72°-73° C.

Workup

  1. temperatureThe mixture is heated to 50°-60° C.
  2. temperatureThe mixture is heated
  3. temperatureunder reflux
  4. temperatureboiling is maintained for 15 minutes
  5. temperatureThe mixture is cooled
  6. temperatureThe mixture is again heated
  7. temperatureunder reflux for 30 minutes
  8. temperaturecooled
  9. customat 60°-70° C
  10. temperatureThe whole is then heated
  11. temperatureunder reflux for 30 minutes
  12. temperaturecooled
  13. filtrationfiltered
  14. customthe precipitate obtained
  15. filtrationis filtered off
  16. dissolutionredissolved cold in dilute sodium bicarbonate solution
  17. washthis solution is washed with methylene chloride
  18. filtrationfiltered

Sources & evidence

ORD record
ord-45fb7da3caf04a29bbc4d877f77ce9ad
Source dataset
uspto-grants-1979_04
Patent number
US04151300

Linked notes

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