Phosgene → HCID 66969259, compound

HRID 1470822Notes

Reaction equation

HRID 1470822 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-c442e74019a840bcb3db598f9c502670
Source dataset
uspto-grants-2015_04
Patent number
US09006468B2

Reaction notes

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