Chloroacetic Acid → Acetic acid, [(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)thio]-

HRID 1752788Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([SH:12])[N:11]=[C:4]2[N:3]=1.[OH-].[Na+].Cl[CH2:16][C:17]([OH:19])=[O:18].Cl>O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12][CH2:16][C:17]([OH:19])=[O:18])[N:11]=[C:4]2[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-thiol (1.0 g, 5.6 mmol), sodium hydroxide (0.44 g, 11.1 mmol), and water (22 mL) was added to a 100 mL RBF with a magnetic stirring bar. The flask was fitted with a condenser, and the mixture was warmed to reflux in a 120° C. oil bath for 30 min. The mixture was removed from the oil bath and allowed to cool, and chloroacetic acid (0.525 g, 5.6 mmol) was added. Warming to reflux was continued for 6 h. The mixture was allowed to cool to ambient temperature, and the pH was adjusted to 2 with 1 M aqueous hydrochloric acid (5 mL). A solid precipitate was isolated by filtration, rinsed with 1 M hydrochloric acid (2 mL) and water (5 mL), and allowed to dry. The title compound was obtained as a tan solid (1.16 g, 88% yield). 1H NMR (DMSO-d6, 400 MHz) δ ppm: 12.85 (br s, 1H), 7.12 (s, 1H), 4.08 (s, 2H), 2.66 (s, 3H), 2.54 (s, 3H).

Workup

additionwas added to a 100 mL RBF with a magnetic stirring bar
customThe flask was fitted with a condenser
temperaturethe mixture was warmed
customThe mixture was removed from the oil bath
temperatureto cool
temperatureWarming
temperatureto reflux
temperatureto cool to ambient temperature
customA solid precipitate was isolated by filtration
washrinsed with 1 M hydrochloric acid (2 mL) and water (5 mL)
customto dry

Sources & evidence

ORD record: ord-01cd3b90424b419aa2e19a397d3e54cc
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163027B2

Reaction notes

Loading…