Chloroacetic Acid → HCID 178526174, compound

HRID 2052393Notes

Reaction equation

HRID 2052393 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+].Cl>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

8

Reactant 6

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 76093,4-Dichlorobenzyl chlorideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 2723790Thiourea

Product 1

HCID 178526174HCID 178526174, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

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

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 30 minutes
  3. customis run in at 60°-70° C.
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 15 minutes
  6. customis run in at 60°-70° C.
  7. temperaturethe mixture is maintained
  8. temperatureunder reflux for 1 hour
  9. extractionextracted with ether
  10. washthe extract is washed with water
  11. customdried
  12. customevaporated
  13. filtrationfiltered off

Sources & evidence

ORD record
ord-8f0b0d75c23b4944af7234bfee52b06f
Source dataset
uspto-grants-1980_01
Patent number
US04183951

Reaction notes

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