2,6-Dimethylphenol → 1-(4-Hydroxy-3,5-dimethylphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

HRID 1616986Notes

Reaction equation

HRID 1616986 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].OC1C=CC([N:17]2[C:21](=[O:22])[N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19](=[O:29])[NH:18]2)=CC=1>>[OH:9][C:3]1[C:4]([CH3:8])=[CH:5][C:6]([N:17]2[C:21](=[O:22])[N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19](=[O:29])[NH:18]2)=[CH:7][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 113352,6-DimethylphenolHCID 672581691-(4-Hydroxyphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Product 1

HCID 672585901-(4-Hydroxy-3,5-dimethylphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Procedure

Compound 30 was prepared from 2,6-dimethylphenol in the same manner of compound 27, and was obtained as white solids (61%). 1H NMR (300 MHz, DMSO-d6): δ 11.32 (br s, 1H), 8.42 (s, 1H), 7.53-7.39 (m, 5H), 7.14 (d, J=1.8 Hz, 1H). 13C NMR (75 MHz, DMSO-d6): δ 152.07, 151.38, 129.58, 127.13, 125.61, 121.94, 121.48, 17.43. HRMS: calcd for C16H15N3O3 (MH+) 298.1186. found 298.1184.

Sources & evidence

ORD record
ord-198464b6ca1a4f698c0f43cbd4e7422d
Source dataset
uspto-grants-2014_07
Patent number
US08765920B2

Reaction notes

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