Ethyl Acetate → 1-(2,4-Difluorophenyl)-1-(6-cyanobenzothiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

HRID 265329Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]([C:20]1[S:21][C:22]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:23]=2[N:24]=1)([OH:19])[CH2:17]Cl.C(OCC)(=O)C>CN(C)C=O.O>[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]([C:20]1[S:21][C:22]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:23]=2[N:24]=1)([OH:19])[CH2:17][N:3]1[CH:7]=[N:6][CH:5]=[N:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (440 mg) was suspended in dimethylformamide (10 ml), and 1,2,4-triazole (948 mg) was added to the suspension, to which a solution of 1-(2,4-difluorophenyl)-1-(6-cyanobenzothiazol-2-yl)-2-chloro-ethanol (1.49 g) in dimethylformamide (10 ml) was added. The mixture was heated at 60° C. for 4 hours. After the liquid reaction mixture was cooled to room temperature, ethyl acetate and water were added thereto. An organic layer separated was washed three times with water and then dried over magnesium sulfate, and the solvent was distilled out. The residue was recrystallized from dichloromethane-diisopropyl ether to obtain the intended compound (1.17 g). Melting point: 170°-172° C.

Workup

additionwas added
customAfter the liquid reaction mixture
temperaturewas cooled to room temperature
customAn organic layer separated
washwas washed three times with water
dry with materialdried over magnesium sulfate
distillationthe solvent was distilled out
customThe residue was recrystallized from dichloromethane-diisopropyl ether

Sources & evidence

ORD record: ord-8d0902b6b1404b61a3def77b11162b30
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648372

Reaction notes

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