Methyl 4-chloroacetoacetate → Methyl 2-(2-amino-1,3-thiazol-4-yl)acetate hydrochloride
Reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[NH2:10][C:11]([NH2:13])=[S:12]>C1COCC1>[ClH:1].[NH2:13][C:11]1[S:12][CH:2]=[C:3]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[N:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 4-chloro-acetoacetate (4.0 g, 27 mmol) in 50 mL of THF was added thiourea (2.0 g, 27 mmol) and the resulting suspension was stirred at reflux for 5 h. The mixture was allowed to cool to room temperature. The white solid was filtered off and washed with ether to afford 5.0 g (90%) of the title compound. 1H NMR (D2O) δ 6.6 (broad s, 1H), 3.7 (broad s, 2H), 3.6 (broad s, 3H). MS (NH3 --CI) 173 (M+H)+ (100%).
Workup
- temperatureat reflux for 5 h
- filtrationThe white solid was filtered off
- washwashed with ether
Sources & evidence
- ORD record
- ord-8e6cc127ed63484c9074aa73e00de5c1
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849693
Reaction notes
Loading…