Acetohydroxamic Acid → 1,2-Benzoxazol-3-amine

HRID 2089128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2089128
[OH:1][NH:2][C:3](=O)[CH3:4].C[C:7]([O-])([CH3:9])[CH3:8].[K+].[C:12](O[Na])([CH3:15])(C)C.C(O[K])CCC.C[N:25]1C(=O)CCC1>CS(C)=O.CN(C=O)C>[NH2:25][C:3]1[C:4]2[CH:12]=[CH:15][CH:8]=[CH:7][C:9]=2[O:1][N:2]=1

Komponenten

8

Edukt 5

HCID 1990Acetohydroxamic AcidHCID 13387N-methyl-2-pyrrolidoneHCID 23665647Potassium tert-butoxideHCID 178418730sodium 2-methylpropan-2-olateHCID 178454393potassium butan-1-olate

Produkt 1

HCID 27797491,2-Benzoxazol-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Commercially available N-hydroxy-acetamide (XVI) is reacted with a suitable substituted fluorobenzonitrile (III), in the presence of an organic base such as t-BuOK, t-BuONa or n-BuOK, in an organic solvent such as DMF, DMSO or NMP, at a temperature in the range of about 80° C. to about 120° C., to yield the corresponding amino-benzoisoxazole (XVII). Amino-bezoisoxazole (XVII) is reacted with glyoxylic acid (V), in the presence of a reducing reagent such as NaBH4, NaBH3CN or NaBH(OAc)3, in an organic solvent such as MeOH, EtOH or IPA with catalytic amount of acid such as acetic acid, trifluoroacetic acid or formic acid, at a temperature in the range of 25° C. to about 60° C., to yield the corresponding acid (XVIII).

Quellen und Nachweise

ORD-Eintrag
ord-a3e41cb4495643fe8c45b67f78c5347a
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436023B2

Notizen zur Reaktion

Wird geladen…