Ethanethiol → 1,2,4-Triazolo(3,4-a)phthalazine, 6-(ethylthio)-3-phenyl-

HRID 2232225Notes

Reaction equation

[H-].[Na+].[CH2:3]([SH:5])[CH3:4].Cl[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2=[N:17][N:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]2[N:8]=1>CN(C)C=O>[CH2:3]([S:5][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2=[N:17][N:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]2[N:8]=1)[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

50% Sodium hydride in mineral oil (1 g) is suspended in anhydrous dimethylformamide (50 ml) and stirred for 10 minutes. Then a solution of ethanethiol (1.5 ml) in anhydrous dimethylformamide (10 ml) is slowly added thereto and the resulting mixture is stirred at room temperature for 30 minutes. Finally 6-chloro-3-phenyl-1,2,4-triazolo[3,4-a]phthalazine (5.9 g) is added and the reaction mixture is heated at 50° C. for five hours. The solvent is evaporated off under vacuum and the obtained residue is washed a few times with water and then is crystallized from isopropanol yielding 4.7 g of the compound of the title. M.p. 190°-91° C.

Workup

stirringthe resulting mixture is stirred at room temperature for 30 minutes
customThe solvent is evaporated off under vacuum
washthe obtained residue is washed a few times with water
customis crystallized from isopropanol yielding 4.7 g of the compound of the title

Sources & evidence

ORD record: ord-029b5507b09c49b4981945f6d1b69230
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788186

Reaction notes

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