2-Mercaptoethanol → 1,4-Oxathiin-3-carboxamide, 5,6-dihydro-2-methyl

HRID 261766

Reaktionsgleichung

Reaktionsgleichung von HRID 261766
[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]

Komponenten

5

Edukt 3

HCID 15672-MercaptoethanolHCID 80077AcetoacetamideHCID 3017751Butanamide, 2-chloro-3-oxo-

Produkt 1

HCID 155633381,4-Oxathiin-3-carboxamide, 5,6-dihydro-2-methyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Quellen und Nachweise

ORD-Eintrag
ord-608e27af385d42f48f7fbd3ab8549040
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152334

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