4-Chlorophenol → 1-(2-Hydroxy-5-chlorophenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

HRID 1616989Notes

Reaction equation

HRID 1616989 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.OC1C=CC([N:16]2[C:20](=[O:21])[N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18](=[O:28])[NH:17]2)=CC=1>>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N:16]1[C:20](=[O:21])[N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18](=[O:28])[NH:17]1

Participants

3

Reactant 2

HCID 46844-ChlorophenolHCID 672581691-(4-Hydroxyphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Product 1

HCID 672561471-(2-Hydroxy-5-chlorophenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Procedure

Compound 34 was prepared from 4-chlorophenol in the same manner of compound 27, and was obtained as white solids (56%). 1H NMR (300 MHz, Methanol-d4): δ 7.75 (d, J=3.0 Hz, 1H), 7.52-7.46 (m, 4H), 7.38 (m, 1H), 7.08 (dd, J=1.8, 8.7 Hz, 1H), 6.88 (d, J=8.7 Hz, 1H). 13C NMR (75 MHz, DMSO-d6): δ 153.70, 152.32, 132.28, 129.63, 128.93, 128.19, 127.12, 126.41, 126.23, 124.62, 123.70, 118.20. HRMS: calcd for C14H10ClN3O3 (MH+) 304.0483. found 304.0487.

Sources & evidence

ORD record
ord-b0c0a5c964704259b52f949ad12b98bc
Source dataset
uspto-grants-2014_07
Patent number
US08765920B2

Reaction notes

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