Potassium Carbonate → HCID 59655024, compound

HRID 2053425Notes

Reaction equation

HRID 2053425 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[CH:11][C:10]=1[NH:17]C(=O)C(F)(F)F)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:17][C:10]1[CH:11]=[CH:12][C:13]([CH:15]=[CH2:16])=[CH:14][C:9]=1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59655009N-(2-benzoyl-4-vinylphenyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 59655024HCID 59655024, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-(2-Benzoyl-4-vinylphenyl)-2,2,2-trifluoroacetamide (b) (0.32 g, 1.0 mmol) was dissolved in a mixture of methanol (38 mL) and water (2.3 mL) and potassium carbonate (0.7 g, 5 mmol) was added. After stirring overnight at room temperature, the mixture was concentrated. Water (20 mL) was added to the residue and the mixture was extracted with chloroform (3×50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel [hexanes:ethyl acetate (9:1)] to produce 2-amino-5-vinylbenzophenone (c) (0.2 g, 90%). 1H NMR (300 MHz, CDCl3) δ 7.70-7.60 (m, 2H), 7.60-7.40 (m, 5H), 6.72 (d, J=10 Hz, 1H), 6.65 (dd, J=11, 19.6 Hz, 1H), 6.16 (s, br, 2H), 5.56 (d, J=19.6 Hz, 1H), 5.03 (d, J=11 Hz,1H). MS: 224.2 (M+H).

Workup

  1. additionwas added
  2. concentrationthe mixture was concentrated
  3. additionWater (20 mL) was added to the residue
  4. extractionthe mixture was extracted with chloroform (3×50 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel [hexanes:ethyl acetate (9:1)]

Sources & evidence

ORD record
ord-5449e4911ea14da89bd20e70d253a9ea
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

Loading…