Hydrochloric Acid → N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

HRID 1454285Notes

Reaction equation

HRID 1454285 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.N1C=CC=CC=1.[C:22](Cl)(=[O:24])[CH3:23].Cl>CCCCCC.C(OCC)(=O)C.C(Cl)Cl>[C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:11])([F:12])[F:13])[CH:7]=1)(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 22393536N-(5-Amino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 22393509N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

N-(5-Amino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (3.27 gm 14.99 mmol) was taken up on anhydrous DCM (75 mL) and cooled to 0EC. Pyridine (3.56 g, 44.97 mmol, 3.64 mL) was added followed by a slow addition of acetyl chloride (1.18 g, 14.99 mol, 1.07 mL). The reaction was allowed to warm to room temp and stir for 30 min. The reaction mixture poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane/ethyl acetate) Yield 2.93 g. 1H NMR (CDCl3, 300 MHz) δ 2.13 (s, 3H), 2.23 (s, 3H), 7.25 (d, J=9 Hz, 1H), 7.23 (d, J=9 Hz, 1H), 7.61 (s, 1H).

Workup

  1. temperaturecooled to 0EC
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-4216186023944fc691ab4754aa65d84f
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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