Hydrogen Peroxide → 5-amino-3-methylisothiazole-4-carbonitrile

Temperature

60 °C

To a stirred solution of (2E)-3-amino-2-cyanobut-2-enethioamide (method 3) (111 g, 0.78 mol) in methanol (2 L) was added dropwise 200 ml of 35% hydrogen peroxide over a period of 30 min. After the completion of the addition the mixture was stirred at 60° C. for 3 h after which the TLC showed the completion of the reaction. The reaction mixture was evaporated to 300 ml in a rotary evaporator and cooled in an ice-bath. The crystallized product was filtered off and washed with isopropyl alcohol (100 ml) and dried in vacuum at 50° C. overnight to provide 5-amino-3-methylisothiazole-4-carbonitrile (105.63 g, 96%) as a light yellow crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 3H), 8.00 (bs, 2H).

1. additionAfter the completion of the addition the mixture
2. customthe completion of the reaction
3. customThe reaction mixture was evaporated to 300 ml in a rotary evaporator
4. temperaturecooled in an ice-bath
5. filtrationThe crystallized product was filtered off
6. washwashed with isopropyl alcohol (100 ml)
7. customdried in vacuum at 50° C. overnight

ORD record

ord-b8387002c57c4f798a8f130b75631399

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07498333B2