Hydrogen Peroxide → 5-amino-3-methylisothiazole-4-carbonitrile
Reaction equation
[NH2:1]/[C:2](/[CH3:9])=[C:3](\[C:7]#[N:8])/[C:4](=[S:6])[NH2:5].OO>CO>[NH2:5][C:4]1[S:6][N:1]=[C:2]([CH3:9])[C:3]=1[C:7]#[N:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of (2E)-3-amino-2-cyanobut-2-enethioamide (method 3) (6.83 g, 48.4 mmol) in methanol (300 mL) was added dropwise 13.6 mL (124 mmoL) of 30% hydrogen peroxide. The mixture was stirred at 60° C. for 4 h and evaporated to 60 mL in a rotary evaporator and cooled in an ice-bath. The crystallized product was filtered off and recrystallized from EtOAc to provide the pure product 5-amino-3-methylisothiazole-4-carbonitrile (5.41 g, 80%) as a white crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 3H), 8.00 (bs, 2H).
Workup
- customevaporated to 60 mL in a rotary evaporator
- temperaturecooled in an ice-bath
- filtrationThe crystallized product was filtered off
- customrecrystallized from EtOAc
Sources & evidence
- ORD record
- ord-e0f1da479c8b47ec961c75f0b1292d85
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498333B2
Reaction notes
Loading…