Sulfuric Acid → 4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-3-hydroxymethyl-5-methyl[1,2,4]triazole

HRID 963046

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2CN=1.S(=O)(=O)(O)O.N([O-])=[O:30].[Na+].[C:33](=[O:36])([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:14]1[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=1[N:12]1[C:20]([CH3:23])=[N:21][N:22]=[C:11]1[CH2:33][OH:36])=[O:30]

Participants

Conditions

Temperature: 90 °C

Procedure

4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (34.3 g) was added to water (500 ml), and conc. sulfuric acid (74 ml) was dropwise added with vigorous stirring. The mixture was further stirred at 90° C. for 1 hour, and sodium nitrite (74 g) was added. Then, potassium carbonate was added to the reaction mixture to make the mixture alkaline. The mixture was extracted with ethyl acetate and washed with water. The mixture was dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethyl acetate-diisopropyl ether to give 26.06 g of 4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-3-hydroxymethyl-5-methyl[1,2,4]triazole.

Workup

additionwas dropwise added with vigorous stirring
extractionThe mixture was extracted with ethyl acetate
washwashed with water
dry with materialThe mixture was dried over magnesium sulfate
customThe solvent was evaporated
customthe residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-c5ede82cc0c54fdcacd312e6d0ac02fa
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760032

Linked notes

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