Water → 5-[4-(4-Chlorobenzyloxy)benzyl]thiazolidine-2,4-dione

HRID 326157

Reaction equation

Br[CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[C:3]([OH:5])=O.[NH2:22][C:23](N)=[S:24].[OH2:26]>CS(C)=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH:2]3[S:24][C:23](=[O:26])[NH:22][C:3]3=[O:5])=[CH:8][CH:9]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

In 2 ml of dimethylsulfoxide are dissolved 200 mg of 2-bromo-3-[4-(4-chlorobenzyloxy)phenyl]propionic acid and 100 mg of thiourea and the solution is heated at 110° C. for 3 hours. Then, after 0.5 ml of water is added, the solution is further heated for 5 hours. Then, 10 ml of water is added and the resulting crystals are recovered by filtration and recrystallized from benzene-n-hexane (1:1). By the above procedure is obtained 170 mg of 5-[4-(4-chlorobenzyloxy)benzyl]thiazolidine-2,4-dione.

Workup

temperaturethe solution is further heated for 5 hours
filtrationthe resulting crystals are recovered by filtration
customrecrystallized from benzene-n-hexane (1:1)

Sources & evidence

ORD record: ord-048413fed7e74475983be6d763a6edda
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04444779

Linked notes

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