3,4-Dichlorophenylacetic acid → HCID 85074710, compound

HRID 1058639Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].O[C:14](=[C:21]1[S:25][C:24](=[O:26])[NH:23][C:22]1=[O:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH:14]=[C:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

3,4-Dichlorophenylacetic acid was dissolved in SO2Cl2 followed by addition of a few drops of DMF. This resulting mixture was heated to 80 ° C for 15-30 min. followed by concentration of the reaction mixture under reduced pressure. The residue was dissolved in THF and slowly added to a solution of 5-(hydroxybenzylidene)thiazolidine-2,4-dione (1.5 eq.) and TEA (1.5 eq.) in THF. The resulting reaction was stirred for 1-2 h at which time the solid was filtered off and filtrate was concentrated under reduced pressure to yield light yellow solid. The solid was dissolved in EtOAc followed by washing with sat. aq. K2CO3. The organic phase was separated, and dried over Na2SO4 followed by concentration under reduced pressure to yield pure compound.

Workup

customThe resulting reaction
filtrationwas filtered off
concentrationfiltrate was concentrated under reduced pressure
customto yield light yellow solid
washby washing with sat. aq. K2CO3
customThe organic phase was separated
dry with materialdried over Na2SO4
concentrationfollowed by concentration under reduced pressure
customto yield pure compound

Sources & evidence

ORD record: ord-e76cf67aca35445690d7136439dc1666
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

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