Acetohydrazide → HCID 178424792, compound

HRID 1979632Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]=[C:10]=[S:11].[C:12]([NH:15][NH2:16])(=O)[CH3:13]>>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N:9]1[C:12]([CH3:13])=[N:15][N:16]=[C:10]1[SH:11]

Participants

Reactant 2

HCID 14039Acetohydrazide

HCID 879762,6-Xylyl isothiocyanate

Product 1

HCID 178424792HCID 178424792, compound

Procedure

Using the method of Example 1, Part A of U.S. Pat. No. 4,338,453, 2,6-dimethylphenyl isothiocyanate and acethydrazide are reacted to produce 4-(2,6-dimethylphenyl)-5-methyl-4H-1,2,4-triazole-3-thiol which is converted to 4-(2,6-dimethylphenyl)-3-methyl-4H-1,2,4-triazole. This triazole (1.87 g 0.01 mole) in 100 ml of tetrahydrofuran at -60° C. bath temperature is reacted with 6.9 ml of 1.6N n-butyllithium in hexane. The resulting mixture is stirred for fifteen minutes. Then using the procedure of Example 1, Part A above, this anion is reacted with 1-(β-phenethyl)-4-piperidinone to produce the product, which is recrystallized from ethyl acetate-hexane to give the subtitled product, mp 189°-192° C., with a C:H:N ratio of 73.30:7.77:14.27.

Sources & evidence

ORD record: ord-3a00e18f78c1494983bc361edbe55d75
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04481360

Reaction notes

Loading…