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

HRID 265329
Notes
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Reaction equation

HRID 265329 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 105940491-(2,4-Difluorophenyl)-1-(6-cyanobenzothiazol-2-YL)-2-chloroethanol

Product 1

HCID 107861891-(2,4-Difluorophenyl)-1-(6-cyanobenzothiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanolYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

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

  1. additionwas added
  2. customAfter the liquid reaction mixture
  3. temperaturewas cooled to room temperature
  4. customAn organic layer separated
  5. washwas washed three times with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled out
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes