Thioglycolic Acid → 5-(3,5-Dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-2-methylbenzoic acid

HRID 2241892Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:16](=[O:17])[NH:15][C:14](=[O:18])[C:13](C(O)=O)=[N:12]2)[CH:7]=[CH:8][C:9]=1[CH3:10])([OH:3])=[O:2].[OH-].[Na+].SCC(O)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[O:17]=[C:16]1[NH:15][C:14](=[O:18])[CH:13]=[N:12][N:11]1[C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]([CH:5]=1)[C:1]([OH:3])=[O:2]

Participants

Conditions

Temperature: 102.5 °C

Procedure

2-(3-Carboxy-4-methyl-phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (110 gm) was added to 8 volumes of water with 2.4 equivalents of sodium hydroxide and 1.1 equivalents of mercaptoacetic acid. The reaction mixture was heated to reflux (100-105° C.) for approximately 18 hours at which point the reaction was complete by HPLC. 30% Sodium hydroxide and toluene were added and the resulting mixture was stirred. Upon settling a large interface was noted. More water, toluene and some ethyl acetate were added. The interface was minimized. The water layer was separated and treated with 2N HCl. At pH 2 solids precipitated out and the slurry was cooled to <10° C. The solids were filtered off in a slow filtration and dried in a vacuum oven to give 69 gm of the title compound.

Workup

temperatureThe reaction mixture was heated
customThe water layer was separated
additiontreated with 2N HCl
customAt pH 2 solids precipitated out
temperaturethe slurry was cooled to <10° C
filtrationThe solids were filtered off in a slow filtration
customdried in a vacuum oven

Sources & evidence

ORD record: ord-d8357b91bcd84fdf8596fdb3e6e24bb0
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671053B2

Reaction notes

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