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

HRID 1616987Notes

Reaction equation

HRID 1616987 reaction equation
[CH3:1]C1C=CC=C(C)C=1O.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([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:13][CH:12]=1>>[OH:10][C:11]1[CH:12]=[CH:13][C:14]([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)=[C:15]([CH3:1])[CH:16]=1

Participants

3

Reactant 2

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

Product 1

HCID 672580291-(4-Hydroxy-2-methylphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Procedure

Compound 31 was prepared from 2,6-dimethylphenol in the same manner of compound 27, and was obtained as white solids (77%). 1H NMR (300 MHz, DMSO-d6): δ 11.22 (br s, 1H), 9.78 (s, 1H), 7.50-7.49 (m, 4H), 7.40 (m, 1H), 7.25 (d, J=8.4 Hz, 1H), 6.71 (d, J=2.4 Hz, 1H), 6.68 (dd, J=2.4, 8.7 Hz, 1H), 2.19 (s, 3H). 13C NMR (75 MHz, DMSO-d6): δ 158.65, 152.58, 138.57, 132.52, 129.57, 126.99, 126.51, 117.72, 114.19, 18.17. HRMS: calcd for C15H13N3O3 (MH+) 284.1030. found 284.1027.

Sources & evidence

ORD record
ord-2102fcd9388d4f3eb08fc46a60b3f7fe
Source dataset
uspto-grants-2014_07
Patent number
US08765920B2

Reaction notes

Loading…