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

HRID 1527353노트

반응식

HRID 1527353 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
23 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ac1823669f5549fba2051c1fe29970e3
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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