Hydrochloric Acid → 2-{4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-[1,2,4]oxadiazolidine-3,5-dione

HRID 724458Notes

Reaction equation

HRID 724458 reaction equation
[C:1](=[O:6])=[N:2][C:3](Cl)=[O:4].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][NH:36][OH:37])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.O1CCCC1.Cl>O>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][N:36]3[C:3](=[O:4])[NH:2][C:1](=[O:6])[O:37]3)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 119708Isocyanatocarbonyl chlorideHCID 21880682N-{4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-hydroxylamine

Product 1

HCID 99354372-{4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-[1,2,4]oxadiazolidine-3,5-dioneYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(Chlorocarbonyl)isocyanate (0.2 mL, 2.6 mmol) was added dropwise into a cold (−5° C.) mixture of N-{4′-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-hydroxylamine (1.1, 2.6 mmol), and tetrahydrofuran (20.0 mL). The reaction mixture was stirred for 30 minutes, poured into water, acidified with HCl (2 N), and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on acidic silica gel (hexanes/EtOAc 2:1) gave a white solid (0.68 g, 53% yield): mp 196–198; MS m/e 493 (M+);

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography on acidic silica gel (hexanes/EtOAc 2:1)

Sources & evidence

ORD record
ord-559d8750b5d9458bba37d6f2dc4bbc4b
Source dataset
uspto-grants-2006_11
Patent number
US07141672B2

Reaction notes

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