3-Chloro-1,2-propanediol → HCID 58333159, compound

HRID 2405077Notes

Reaction equation

HRID 2405077 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.Cl[CH2:19][CH:20]([OH:23])[CH2:21][OH:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3([C:10]([F:13])([F:11])[F:12])[O:23][CH:20]([CH2:21][OH:22])[CH2:19][O:14]3)=[N:6][C:5]=2[CH:15]=1

Participants

6

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 11430Potassium CarbonateHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 58333159HCID 58333159, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(5,6-DiChloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (503 mg), 3-chloro-1,2-propan-diol (393 mg) and potassium carbonate (491 mg) were dissolved in DMF (5 mL). The reaction mixture was stirred for 18 hrs at ambient temperature, then diluted with ethyl acetate (50 mL), washed with water (50 mL) and brine (2×20 mL). The extracts were dried over Na2SO4, filtered, concentrated, and purified by column chromatography (SiO2; 40% ethyl acetate/hexanes), followed by washing solid with CH2Cl2/hexanes to yield the title compound as an off-white solid.

Workup

  1. washwashed with water (50 mL) and brine (2×20 mL)
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (SiO2; 40% ethyl acetate/hexanes)
  6. washby washing solid with CH2Cl2/hexanes

Sources & evidence

ORD record
ord-8a7ad4efcdeb41a198c8cfeefff4e2c6
Source dataset
uspto-grants-2014_08
Patent number
US08802865B2

Reaction notes

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