Hydrochloric Acid → HCID 12810954, compound

HRID 2166539Notes

Reaction equation

HRID 2166539 reaction equation
Cl[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)[C:3](OCC)=[O:4].[NH2:16][C:17](N)=[S:18].Cl.[OH2:21]>C(OCCO)C>[CH3:15][C:10]1[CH:9]=[C:8]([CH:2]2[S:18][C:17](=[O:21])[NH:16][C:3]2=[O:4])[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723790ThioureaHCID 10799298Ethyl 2-chloro-2-(3,4-dimethylphenyl)acetate

Product 1

HCID 12810954HCID 12810954, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

2.26 g of ethyl α-chloro-α-(3,4-dimethylphenyl)acetate and 910 mg of thiourea, in 15 ml of ethylene glycol monoethyl ether, are stirred under reflux for 2 hours. Then, 1 ml of concentrated HCl is added and the mixture is further heated under reflux for 3.5 hours. After cooling, water is added and extraction is carried out with ethyl acetate. The extract is washed with water and dried (MgSO4). After the solvent is distilled off, column chromatography is carried out on the oily residue with 100 g of silica gel. The eluate with chloroform-ethyl acetate (5:1) yields crystals of 5-(3,4-dimethylphenyl)thiazolidine-2,4-dione 1.32 g (60%). Recrystallization from cyclohexane-ethyl acetate gives colorless prisms, m.p. 121°-122° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturethe mixture is further heated
  3. temperatureunder reflux for 3.5 hours
  4. temperatureAfter cooling
  5. extractionextraction
  6. washThe extract is washed with water
  7. dry with materialdried (MgSO4)
  8. distillationAfter the solvent is distilled off

Sources & evidence

ORD record
ord-565dcff0765548df9891ad7756aad189
Source dataset
uspto-grants-1983_06
Patent number
US04387101

Reaction notes

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