4-Fluoro-2-methylaniline → N-Benzyl-2-(4-fluoro-2-methyl-phenylamino)acetamide

HRID 1350093

反応式

HRID 1350093 の反応式
[CH2:1]([NH:8][C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([CH3:30])[CH:24]=1>CN(C=O)C>[CH2:1]([NH:8][C:9](=[O:12])[CH2:10][NH:27][C:26]1[CH:28]=[CH:29][C:23]([F:22])=[CH:24][C:25]=1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 679824-Fluoro-2-methylanilineHCID 81531DiisopropylethylamineHCID 96233N-Benzyl-2-chloroacetamide

生成物 1

HCID 17954343N-Benzyl-2-(4-fluoro-2-methyl-phenylamino)acetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of N-benzyl-2-chloroacetamide (17.8 g), DIPEA (19.5 mL) and 4-fluoro-2-methyl-aniline (10.6 mL) in anhydrous DMF (174 mL) was stirred at 100° C. for 40 hours under a Nitrogen atmosphere. After cooling to r.t., the dark solution was partitioned between AcOEt (200 mL) and water (200 mL). The separated aqueous phase was extracted with further AcOEt (3×200 mL). The combined organic extracts were washed with water (200 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography (CH/AcOEt 2:8) to give a dark solid, which was triturated with CH to give the title compound as a beige solid (16.2 g).

後処理

  1. temperatureAfter cooling to r.t.
  2. customthe dark solution was partitioned between AcOEt (200 mL) and water (200 mL)
  3. extractionThe separated aqueous phase was extracted with further AcOEt (3×200 mL)
  4. washThe combined organic extracts were washed with water (200 mL)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (CH/AcOEt 2:8)
  8. customto give a dark solid, which
  9. customwas triturated with CH

出典と根拠

ORDレコード
ord-32be2152ebde416aaec4707f2bd9919e
出典データセット
uspto-grants-2007_05
特許番号
US07214680B2

関連ノート

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