Hydrochloric Acid → 5-(2-Chloro-6-methoxyphenyl)-1,3-thiazolidine-2,4-dione

HRID 2290535Notes

Reaction equation

HRID 2290535 reaction equation
Cl[CH:2]([C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[O:14][CH3:15])[C:3]([O:5]C)=O.[NH2:16][C:17](N)=[S:18].C([OH:22])C.Cl>C(OCC)(=O)C.O>[Cl:13][C:12]1[C:7]([CH:2]2[S:18][C:17](=[O:22])[NH:16][C:3]2=[O:5])=[C:8]([O:14][CH3:15])[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 2723790ThioureaHCID 13731103HCID 13731103, compound

Product 1

HCID 137311045-(2-Chloro-6-methoxyphenyl)-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl alpha-chloro-alpha-(6-chloro-2-methoxyphenyl)acetate (1.37 g, 5.5 mmoles), thiourea (0.84 g, 10.0 mmoles) and ethanol (10 ml) was refluxed for 16 hours. Concentrated hydrochloric acid (4 ml) was added to the mixture and refluxing continued for an additional 16 hours. An additional 2 ml of concentrated hydrochloric acid was added and the mixture refluxed for 16 more hours. The yellow solution was then cooled to room temperature and poured into 150 ml of water. The title product was isolated by extraction of the aqueous mixture with ethyl acetate (2×150 ml). The extract was washed with water (1×50 ml) and brine (1×50 ml), then dried (MgSO4) and concentrated in vacuo to a brown oil (0.91 g). Trituration of the oil in hexane (50 ml) gave a solid which was recrystallized from ethanol-water (1:1) as a white solid, 0.0719 g. M.P. 195°-197° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperaturerefluxing
  3. temperaturethe mixture refluxed for 16 more hours

Sources & evidence

ORD record
ord-7498fa59d5fe416495889d7d79f915e6
Source dataset
uspto-grants-1986_10
Patent number
US04617312

Reaction notes

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