2-Chloroethanol → HCID 86614857, compound

HRID 2037231Notes

Reaction equation

HRID 2037231 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:5]1[NH:9][C:8]2[CH:10]=[C:11]([C:16]([F:19])([F:18])[F:17])[C:12]([C:14]#[N:15])=[CH:13][C:7]=2[N:6]=1)=[O:4].Cl[CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.C(OCC)C>[F:19][C:16]([F:17])([F:18])[C:11]1[C:12]([C:14]#[N:15])=[CH:13][C:7]2[N:6]=[C:5]([C:3]3([C:2]([F:20])([F:1])[F:21])[O:25][CH2:24][CH2:23][O:4]3)[NH:9][C:8]=2[CH:10]=1

Participants

7

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 86614855HCID 86614855, compound

Product 1

HCID 86614857HCID 86614857, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2,2,2-Trifluoro-acetyl)-6-trifluoromethyl-1H-benzoimidazole-5-carbonitrile (0.50 g; 1.5 mmol), was dissolved in DMF (4 mL), then treated with 2-chloroethanol (0.35 mL; 5.2 mmol) and potassium carbonate (0.73 g; 5.3 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then diluted with ethyl acetate (40 mL) and diethyl ether (40 mL), washed with water (50 mL) and brine (3×30 mL), then dried over Na2SO4. The reaction mixture was filtered, concentrated to yield a light brown solid, which was purified by column chromatography (SiO2; 100% ethyl acetate) to yield the title compound as a light yellow solid.

Workup

  1. washwashed with water (50 mL) and brine (3×30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. customto yield a light brown solid, which
  6. customwas purified by column chromatography (SiO2; 100% ethyl acetate)

Sources & evidence

ORD record
ord-e3cf5e8ee0164dba8d1802730c396d6a
Source dataset
uspto-grants-2013_11
Patent number
US08575206B2

Reaction notes

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