Bromine → 3-(Methoxymethyl)-1,2,4-thiadiazol-5-amine

Temperature

5 °C

To a solution of 2-methoxy-acetamidine hydrochloride (4.66 g, 0.037 mol) in methanol (20 mL) at 0° C. under vigorous stirring was added dropwise bromine (1.90 mL, 0.037 mol) and a 5.4M sodium methylate solution in methanol (13.7 mL, 0.037 mol) simultaneously over 30 min maintaining a slight bromine excess by color. To the resulting nearly colorless suspension was added dropwise a solution of potassium thiocyanate (3.64 g, 0.037 mol) in methanol (20 mL) over 10 min at 0-10° C. The resulting mixture was stirred for 2 h at 0-10° C. and filtered. The isolated material was washed with methanol and dried which afforded a brown solid which was purified by flash chromatography (silica gel 60, 5% methanol/diethyl ether) and crystallized from diethyl ether/hexanes which afforded 3-methoxymethyl-[1,2,4]thiadiazol-5-ylamine (3.25 g, 60%) as a light yellow solid.

1. filtrationfiltered
2. washThe isolated material was washed with methanol
3. customdried which
4. customafforded a brown solid which
5. customwas purified by flash chromatography (silica gel 60, 5% methanol/diethyl ether)
6. customcrystallized from diethyl ether/hexanes which

ORD record

ord-0a5cb7af2a87404d9ad64641dcf6e21a

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741327B2