Chloroacetic Acid → HCID 178526174, compound

HRID 2285932Notes

Reaction equation

HRID 2285932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Cl.NC(N)=[S:13].[OH-].[Na+].Cl[CH2:18][C:19]([OH:21])=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][CH2:18][C:19]([OH:21])=[S:13]

Participants

7

Reactant 5

HCID 300Chloroacetic AcidHCID 76093,4-Dichlorobenzyl chlorideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 2723790Thiourea

Product 1

HCID 178526174HCID 178526174, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A mixture of 19.5 (0.1 mol) of 3,4-dichlorobenzyl chloride and 7.6 g (0.1 mol) of thiourea in 50 ml of water is heated under reflux for 30 minutes, with stirring, and then, at 60°-70° C., a solution of 16 g (0.4 mol) of NaOH in 25 ml of water is run in; the mixture is heated under reflux for 15 minutes and a solution of 15 g (0.15 mol) of chloroacetic acid, 7 g of sodium carbonate and 50 ml of water are run in at 60°-70° C., and the reaction mixture is maintained under reflux for 1 hour. The mixture is acidified, whilst cold, with concentrated HCl, and is extracted with ether, and the ether extract washed with water, dried and evaporated. The residue is taken up in petroleum ether and the product filtered off. 21 g (yield 83%) of the stated product are obtained. Melting point 63°-64° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 minutes
  3. customat 60°-70° C.
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 15 minutes
  6. customare run in at 60°-70° C.
  7. temperaturethe reaction mixture is maintained
  8. temperatureunder reflux for 1 hour
  9. extractionwhilst cold, with concentrated HCl, and is extracted with ether
  10. extractionthe ether extract
  11. washwashed with water
  12. customdried
  13. customevaporated
  14. filtrationthe product filtered off

Sources & evidence

ORD record
ord-c72b1ed0e5964a59b4f8c12c6b6a8e71
Source dataset
uspto-grants-1982_04
Patent number
US04325964

Reaction notes

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