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

HRID 1454285노트

반응식

HRID 1454285 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4216186023944fc691ab4754aa65d84f
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07479495B2

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