Iodine → N-[2-(3-Iodo-7-methoxy-1-naphthyl)ethyl]acetamide

HRID 1856905노트

반응식

HRID 1856905 반응식
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[C:15]2[CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])=[CH:10][CH:9]=1.[I:24]I.I>O.C(O)(=O)C>[I:24][C:13]1[CH:14]=[C:15]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:7][CH3:6])[CH:17]=2

참가 물질

7

반응물 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 24841Hydrogen iodideHCID 82148Agomelatine

생성물 1

HCID 22133330N-[2-(3-Iodo-7-methoxy-1-naphthyl)ethyl]acetamide

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

반응 조건

온도
65 °C

실험 절차

A solution is formed by adding 46.25 ml of glacial acetic acid and 1.25 ml of concentrated sulphuric acid to 2.5 ml of water. 2.5 g of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide (10.31 mmol) are dissolved in 30 ml of that solution. 2.09 g of iodine (8.25 mmol) and 0.91 g of HIO3 (5.16 mmol) are then added to the reaction mixture, causing a grey precipitate to appear in a solution that has turned red. The reaction mixture is heated for 15 hours at 65° C., 5.14 ml of concentrated hydriodic acid (13.41 mmol) are added and heating is continued for 2 hours. The suspension is then poured into 200 ml of water and the precipitate that forms is filtered off. The precipitate is dissolved in ethyl acetate and washed with 1M NaHCO3, the organic phase is then concentrated, and purified by chromatography on silica gel, using a dichloromethane/methanol mixture, 99.5/0.5, as eluant, to yield the title product.

후처리

  1. customA solution is formed
  2. temperatureheating
  3. filtrationthe precipitate that forms is filtered off
  4. dissolutionThe precipitate is dissolved in ethyl acetate
  5. washwashed with 1M NaHCO3
  6. concentrationthe organic phase is then concentrated
  7. custompurified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-1a4be8483b224d8fbe142c3b128bf815
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06143789

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