Acetic Acid → HCID 86685926, compound

HRID 2277595Notes

Reaction equation

HRID 2277595 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:5]=[CH:6][C:7]=1[F:8].C=O.[C:20](O)(=O)C>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[F:8])[CH2:20][N:11]([C:12](=[O:17])[C:13]([F:14])([F:15])[F:16])[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 86685925HCID 86685925, compound

Product 1

HCID 86685926HCID 86685926, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-[2-(3-Chloro-4-fluoro-phenyl)-ethyl]-2,2,2-trifluoro-acetamide (400 mg, 1.48 mmol) and paraformaldehyde (89 mg, 2.96 mmol) were added sequentially at 0° C. to a solution of acetic acid (3 mL) in sulfuric acid (2 mL). After stirring of the reaction mixture at room temperature for 16 hours, the clear colorless solution was poured into ice-water (20 mL). The mixture was extracted with EtOAc (2×30 mL) and the organic layer was washed with satd. aq. NaHCO3 (20 mL), H2O (2×25 mL), dried over anhy. Na2SO4, filtered and concentrated in vacuo to give the crude title product together with a regioisomer (400 mg) as white solid.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×30 mL)
  2. washthe organic layer was washed with satd
  3. dry with materialaq. NaHCO3 (20 mL), H2O (2×25 mL), dried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ed6e8fc92ae46d7a8eb149f4c056151
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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