2-[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid → 2-[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-2H-[1,2,4]triazine-3,5-dione

HRID 585127Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[C:15](C(O)=O)=[N:14]2)=[CH:8][C:7]=1[CH3:24].C(O)(=S)C>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[O:5][C:6]1[C:7]([CH3:24])=[CH:8][C:9]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[CH:15]=[N:14]2)=[CH:10][C:11]=1[CH3:12]

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 2-[4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (0.3 g) of EXAMPLE 2 and thioacetic acid (0.6 ml) was heated at 170° C. for 4 h. The mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, and dried with sodium sulfate to afford a crude brown oil (0.6 g). Chromatography on silica gel, eluting with ethyl acetate and hexanes, gave the title compound (160 mg) as a yellow foam.

Workup

washwashed with saturated sodium bicarbonate
dry with materialdried with sodium sulfate
customto afford a crude brown oil (0.6 g)
washChromatography on silica gel, eluting with ethyl acetate and hexanes

Sources & evidence

ORD record: ord-584e0a7d99a94ac993fafb74d362de7b
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930107B2

Reaction notes

Loading…