Water → N-(4-Methylthiazol-2-yl)acetamide
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[C:8](Cl)(=[O:10])[CH3:9].O>N1C=CC=CC=1>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][C:8](=[O:10])[CH3:9])[S:3][CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Amino-4-methylthiazole (10.0 g, 87.6 mmol) is dissolved in dry pyridine (75 ml) at room temperature. This solution is then treated dropwise with acetyl chloride (6.3 ml, 87.6 mmol). After 2 hours, the reaction mixture is poured into water (1000 ml), and extracted with ethyl acetate (3×250 ml). The combined organic layers are washed with water (2×200 ml), brine (200 ml), dried over MgSO4, filtered and concentrated in vacuo. The residue is dissolved in toluene (200 ml) followed by the removal of the solvent in vacuo. The solid thus obtained is dried in vacuo to give the title compound.
Workup
- extractionextracted with ethyl acetate (3×250 ml)
- washThe combined organic layers are washed with water (2×200 ml), brine (200 ml)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- dissolutionThe residue is dissolved in toluene (200 ml)
- customfollowed by the removal of the solvent in vacuo
- customThe solid thus obtained
- customis dried in vacuo
Sources & evidence
- ORD record
- ord-203335b956fb44478464cdd6c17f29fd
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687637B2
Reaction notes
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