Hydrochloric Acid → 2-[4-(Benzyloxy)phenyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

反応式

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:17].[C:18]([N:23]=[C:24](OCC)[CH2:25][CH2:26][CH2:27][CH3:28])(OCC)=[O:19]>>[ClH:17].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][NH2:16])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:18](=[O:19])[NH:23][C:24]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:16]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

反応物 3

HCID 313Hydrochloric Acid

HCID 5613924-Benzyloxyphenylhydrazine

HCID 53930077ethyl N-carbethoxyvalerimidate

生成物 2

HCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

HCID 1357200832-[4-(Benzyloxy)phenyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one収率 9%

実験手順

By the procedure of Example 4, Step C, p-(benzyloxy)phenylhydrazine [generated from the hydrochloride by partitioning between ether and 1N Na2CO3. The p-(benzyloxy)phenylhydrazine hydrochloride was prepared from the corresponding aniline according to H. Stroh and G. Westphal, Chem. Ber., 96, 184 (1963)] was reacted with ethyl N-carbethoxyvalerimidate (from Example 4, Step B). After work-up, the residue was purified by flash chromatography on silica gel to give a 9% yield of the desired compound, homogeneous by TLC in 19.1 CH2Cl2 /CH3OH; mass spectrum (FAB) m/e 324 (M+1)+.