1,3-Dichloroacetone → 4-(Chloromethyl)-2-(propan-2-yl)-1,3-thiazole--hydrogen chloride (1/1)
Reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=[S:5])[NH2:4].[Cl:7][CH2:8][C:9]([CH2:11]Cl)=O.[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[ClH:7].[Cl:7][CH2:8][C:9]1[N:4]=[C:3]([CH:2]([CH3:6])[CH3:1])[S:5][CH:11]=1Participants
5
Procedure
A mixture of 94.0 g (0.91 mol) of 2-methylpropane-thioamide, 115.7 g (0.91 mol) of 1,3-dichloroacetone, and 109.7 g (0.91 mol) of MgSO4 in 1.6 liters of acetone was heated at reflux for 3.5 h. The resulting mixture was allowed to cool, filtered, and the solvent was removed in vacuo to provide the crude desired compound as a yellow oil. 1H NMR (DMSO-d6) δ1.32 (d, J=7 Hz, 6H), 3.27 (heptet, J=7 Hz, 1H), 4.78 (s, 2H), 7.61 (s, 1H). Mass spectrum: (M+H)+ =176.
Workup
- temperaturewas heated
- temperatureat reflux for 3.5 h
- temperatureto cool
- filtrationfiltered
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-a7eb556908204482bceb93a605ec7ad7
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616720
Reaction notes
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