Phosgene → HCID 66969259, compound

HRID 1189522Notes

Reaction equation

HRID 1189522 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[C:24](Cl)(Cl)=[O:25].[H][H]>CCO.[Pd]>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([C:11]2[O:21][C:24](=[O:25])[N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:22])([F:23])[F:1])=[CH:8][CH:7]=3)[N:10]=2)=[CH:17][CH:16]=1)([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 70497840HCID 70497840, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66969259HCID 66969259, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(4-Nitrophenyl)-3-(4-trifluoromethylphenyl) 3H-[1,3,4]oxadiazole-2-one was prepared by treating the corresponding 4-nitrobenzoic acid N′-(4-trifluoromethylphenyl)hydrazide with phosgene, using conditions described by Reimlinger et al. in Chem. Ber. 1970, 103, 1934. The nitro group was then reduced to the amine by treatment with hydrogen and Pd/C in EtOH: mp 160-163° C.; 1H NMR (400 MHz, CDCl3) δ 8.1 (d, J=8.4 Hz, 2H), 7.75 (m, 4H), 6.75 (d, J=8.4 Hz, 2H), 4.1 (br s, 2H); MS m/z 322.6 (MAI).

Sources & evidence

ORD record
ord-e87317dd9a8f400d9dd68e9e43b04ebf
Source dataset
uspto-grants-2014_03
Patent number
US08674109B2

Reaction notes

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