2-Mercaptoethanol → 1,4-Oxathiin-3-carboxamide, 5,6-dihydro-2-methyl
Reaction equation
[C:1]([NH2:7])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].ClC(C(C)=O)C(N)=O.[SH:16][CH2:17][CH2:18]O>O>[CH3:5][C:3]1[O:4][CH2:18][CH2:17][S:16][C:2]=1[C:1]([NH2:7])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The prior art preparation of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxamides (Ia) has been effected by two methods. The first method has included (1) converting acetoacetamide to alphachloroacetoacetamide, (2) reacting this with 2-mercaptoethanol in a mutual solvent in the presence of a base, (3) subjecting the resulting product to acidic conditions whereby it cyclizes with loss of water to form 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxamide (Ia) and (4) isolating said product from the reaction mixture. The second method of preparing same has used alkyl acetoacetate in place of acetoacetamide as a starting material. Thus, from the procedure analogous to the first method described above, the resulting 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboalkoxide (Ib) was converted to 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxamide (Ia).
Sources & evidence
- ORD record
- ord-608e27af385d42f48f7fbd3ab8549040
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04152334
Reaction notes
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