Hydrochloric Acid → HCID 57976187, compound

HRID 1865319Notes

Reaction equation

HRID 1865319 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[NH2:15][C:16]([CH3:22])([CH2:20][OH:21])[C:17](O)=[O:18].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]([CH2:20][OH:21])([CH3:22])[NH:15][C:9]2=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 94309alpha-Methyl-DL-serineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

Product 1

HCID 57976187HCID 57976187, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Chloro-4-isocyanato-2-trifluoromethyl-benzene (4.40 g, 20 mmoL) and 2-amino-3-hydroxy-2-methyl-propionic acid (2.38 g, 20 mmoL) in dioxane (100 mL) was heated at 80° C. for 6 hrs. The reaction was cooled to room temperature and concentrated HCl (˜2 mL) was added and the reaction mixture was heated to refluxed for 4 hrs. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with sat. NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated, then recrystallization was conducted using ethyl acetate as solvent to afford the title compound as a white solid (2.65 g, yield 41%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto refluxed for 4 hrs
  3. customThe solvent was removed
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with sat. NaHCO3, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customrecrystallization

Sources & evidence

ORD record
ord-000649a9374b457888c128a67b04d50f
Source dataset
uspto-grants-2009_12
Patent number
US07626036B2

Reaction notes

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