2-Naphthol → 1-(2-Hydroxynaphtyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

HRID 1616990Notes

Reaction equation

HRID 1616990 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].OC1C=CC([N:19]2[C:23](=[O:24])[N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21](=[O:31])[NH:20]2)=CC=1>>[OH:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]=1[N:19]1[C:23](=[O:24])[N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21](=[O:31])[NH:20]1

Participants

3

Reactant 2

HCID 86632-NaphtholHCID 672581691-(4-Hydroxyphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Product 1

HCID 672582941-(2-Hydroxynaphtyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Procedure

Compound 35 was prepared from 2-naphthol in the same manner of compound 27, and was obtained as white solids (89%). 1H NMR (300 MHz, DMSO-d6): δ 10.94 (br s, 1H), 7.95 (d, J=9.0 Hz, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.58-7.50 (m, 5H), 7.44-7.35 (m, 2H), 7.27 (dd, J=2.4, 9.0 Hz, 1H). 13C NMR (75 MHz, DMSO-d6): δ 154.39, 152.93, 152.16, 133.29, 132.99, 132.18, 129.59, 128.77, 128.58, 128.45, 128.29, 126.88, 124.19, 121.90, 119.38, 114.74. HRMS: calcd for C18H13N3O3 (MH+) 320.103. found 320.1032.

Sources & evidence

ORD record
ord-54f4ce67f85c46dc994a19cf0819f0bd
Source dataset
uspto-grants-2014_07
Patent number
US08765920B2

Reaction notes

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