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

HRID 1071525ノート

反応式

HRID 1071525 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

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 0° C. 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).

後処理

  1. temperatureto warm to room temp
  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

出典と根拠

ORDレコード
ord-4e5752271d6745a3873e46d02b71ad4e
出典データセット
uspto-grants-2005_06
特許番号
US06906067B2

反応ノート

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