Methanol → Methyl {5-[(ethoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl}acetate
Reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[S:11][N:10]=[C:9]([CH2:12][C:13]([OH:15])=[O:14])[N:8]=1)=[O:5])[CH3:2].[CH3:16]O>>[CH3:16][O:14][C:13](=[O:15])[CH2:12][C:9]1[N:8]=[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:11][N:10]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Into a 3 L round bottom flask equipped with mechanical stirrer, thermometer and nitrogen purge was charged 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetic acid (185 g, 0.80 mol, 1.0 eq.) followed by methanol (925 mL) and the resulting solution was cooled to 0° C. To the solution was bubbled in HCl gas for 30 minutes and the thinning slurry was allowed to stir overnight at 20° C. Proton NMR analysis shows complete conversion to the title compound. The solvent was removed by rotary evaporation to 400 mL and then cooled to 0° C. and seeded with pure title compound. The thickening reaction mixture was stirred at 0° C. for two hours and the white solid was collected by vacuum filtration. The solid was dried under high vacuum for 12 hours at 20° C. to give 172.2 grams of the title compound as an off white solid. 1H NMR (CD3OD): δ 1.47 (t, 3H); 3.83 (s, 3H); 3.97 (s, 2H); 4.45 (q, 2H).
Workup
- customInto a 3 L round bottom flask equipped with mechanical stirrer
- customthermometer and nitrogen purge
- customTo the solution was bubbled in HCl gas for 30 minutes
- customThe solvent was removed by rotary evaporation to 400 mL
- temperaturecooled to 0° C.
- customThe thickening reaction mixture
- stirringwas stirred at 0° C. for two hours
- filtrationthe white solid was collected by vacuum filtration
- customThe solid was dried under high vacuum for 12 hours at 20° C.
Sources & evidence
- ORD record
- ord-c03906a02d9348e982713d6ac42dfddb
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06723716B1
Reaction notes
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