Hydrochloric Acid → N-(3-Chloro-2-fluoro-benzyl)-acrylamide

HRID 1527353ノート

反応式

HRID 1527353 の反応式
[F:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].Cl>C1COCC1.CCOC(C)=O>[Cl:10][C:9]1[C:2]([F:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH2:4][NH:5][C:11](=[O:14])[CH:12]=[CH2:13]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 2773614(3-Chloro-2-fluorophenyl)methanamine

生成物 1

HCID 68283248N-(3-Chloro-2-fluoro-benzyl)-acrylamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
23 °C

実験手順

To a solution of 2-fluoro-3-chlorobenzylamine (1 g, 6.27 mmol) and TEA (1.05 mL, 7.52 mmol) in THF (20.9 mL) was added acryloyl chloride (0.61 mL, 7.52 mmol) dropwise and the reaction mixture was stirred at 23° C. for 2 h. The reaction mixture was diluted in EtOAc, HCl 1N was added and the layers separated. The aqueous layer was extracted again with EtOAc and the combined organic layers were dried, filtered and concentrated to dryness. The crude residue was purified by flash column chromatography on silica gel (xyclohexane/EtOAc gradient 100:0 to 1:1) to give the desired material. TLC, Rf (c-hexane/EtOAc 5:5)=0.41; MS (LC/MS): 214.0 [M+H]+; tR (HPLC conditions b): 3.35 min.

後処理

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted again with EtOAc
  3. customthe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude residue was purified by flash column chromatography on silica gel (xyclohexane/EtOAc gradient 100:0 to 1:1)

出典と根拠

ORDレコード
ord-ac1823669f5549fba2051c1fe29970e3
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

読み込み中…