Acetic Acid → 5-[1-(2-Methoxy-2'-trifluoromethyl-biphenyl-4-yl)-methylidene]-2-thioxo-thiazolidin-4-one

HRID 1012213Notes

Reaction equation

[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25].C(O)(=O)C.CC([O-])=O.[Na+]>CCOC(C)=O>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH:16]=[C:7]2[S:1][C:2](=[S:3])[NH:4][C:5]2=[O:6])[CH:13]=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:25])([F:27])[F:26]

Participants

Conditions

Temperature: 95 °C

Procedure

To a flask was added rhodanine (37 mg, 275 μmol), 2-Methoxy-2′-trifluoromethyl-biphenyl-4-carboxaldehyde (70 mg, 250 μmol), acetic acid (4 mL) and NaOAc (60 mg, 3 equiv). The reaction solution was allowed to stir at 95° C. under N2 for 14 h. Additional NaOAc (60 mg, 3 equiv) was added to the solution and stirred at 100° C. for an additional 24 h. The reaction solution was diluted with EtOAc (100 mL), washed with water (50 mL×3), washed with aq NaHCO3 (50 mL×3), dried and concentrated. The crude material was chromatographed (SiO2, Hex:EtOAc 100:0 to 70:30) to yield the intermediate compound. (79 mg, 80%).

Workup

stirringstirred at 100° C. for an additional 24 h
washwashed with water (50 mL×3)
washwashed with aq NaHCO3 (50 mL×3)
customdried
concentrationconcentrated
customThe crude material was chromatographed (SiO2, Hex:EtOAc 100:0 to 70:30)
customto yield the intermediate compound

Sources & evidence

ORD record: ord-07701a008a034e6aa4ff611f4522cfc1
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977489B2

Reaction notes

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