Phosgene → HCID 66969259, compound

HRID 1925434Notes

Reaction equation

HRID 1925434 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 Chemische Berichte 1970, 103, 1934. The nitro group was then reduced to the amine by treatment with hydrogen and Pd/C in EtOH. 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 322.6 (M+H+); mp 160-163° C.

Sources & evidence

ORD record
ord-9df22ba0d58b4e65aa66190999253bae
Source dataset
uspto-grants-2012_05
Patent number
US08178658B2

Reaction notes

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