Acetamidine monohydrochloride → 2,4-dihydro-4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-5-methyl-3H-1,2,4-triazol-3-one

HRID 2286556

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][NH2:25])=[O:23])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl.[C:27](=N)(N)[CH3:28]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:27]([CH3:28])=[N:25][NH:24][C:22]4=[O:23])=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 53 parts of N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide, 53 parts of ethanimidamide hydrochloride and 135 parts of N,N-dimethylformamide is stirred and heated for 3 hours at 130° C. The reaction mixture is cooled and poured onto water. The precipitated product is filtered off, washed with water and with methanol, and crystallized from N,N-dimethylformamide. The product is filtered off and recrystallized from 1,4-dioxane, yielding 19.5 parts of 2,4-dihydro-4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-5-methyl-3H-1,2,4-triazol-3-one; 298.4° C.

Workup

temperatureThe reaction mixture is cooled
additionpoured onto water
filtrationThe precipitated product is filtered off
washwashed with water and with methanol
customcrystallized from N,N-dimethylformamide
filtrationThe product is filtered off
customrecrystallized from 1,4-dioxane

Sources & evidence

ORD record: ord-02a36d50c57b4e41811cf3f377a1d459
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04267179

Linked notes

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