1-Chloro-3-(2-cyanoethylthio)propanone → 3-(2-(Diaminomethyleneamino)thiazol-4-yl)methylthio)propiononitrile
Reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][S:5][CH2:6][CH2:7][C:8]#[N:9].[C:11]([NH:14][C:15]([NH2:17])=[S:16])(=[NH:13])[NH2:12]>CC(C)=O>[C:8]([CH2:7][CH2:6][S:5][CH2:4][C:3]1[N:17]=[C:15]([N:14]=[C:11]([NH2:13])[NH2:12])[S:16][CH:2]=1)#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 8.9 g of 1-chloro-3-(2-cyanoethylthio)propanone in 100 ml of acetone is added 6.3 g of amidinothiourea and the reaction mixture is stirred at 50° C. for 9 hours. Also, the reaction mixture is concentrated under reduced pressure, made basic with saturated sodium carbonate solution, and extracted with chloroformmethanol (10:1) solution (170 ml×2). The combined organic layer is dried over anhydrous magnesium sulfate, and is concentrated in vacuo to give a solid, which is crystallized from acetone-hexane to afford 10.2 g of the title compound, m.p.: 125°-128° C.
Workup
- concentrationAlso, the reaction mixture is concentrated under reduced pressure
- extractionextracted with chloroformmethanol (10:1) solution (170 ml×2)
- dry with materialThe combined organic layer is dried over anhydrous magnesium sulfate
- concentrationis concentrated in vacuo
- customto give a solid, which
- customis crystallized from acetone-hexane
Sources & evidence
- ORD record
- ord-abe8842aea0244f5a2511401f2431421
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04942243
Reaction notes
Loading…