Iodine → 3-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

HRID 1456630

반응식

HRID 1456630 반응식
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][C:2]1=[O:12].C[Si](C)(C)N[Si](C)(C)C.[I:22]I.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[I:22][CH:3]1[CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:1][C:2]1=[O:12]

참가 물질

7

반응물 4

HCID 807IodineHCID 13838HexamethyldisilazaneHCID 24437Sodium SulfiteHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

생성물 1

HCID 110334773-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one수율 60.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
30 °C

실험 절차

A suspension of 34.2 g (212 mmol) of 2,3,4,5tetrahydro-1H-[1]-benzazapin-2-one and 224 mL (171.2 g, 1.06 mol) of hexamethyldisilazane in 400 mL of methylene chloride was heated at reflux for 15 min and cooled to 30° C. Iodine (161.5 g, 636 mmol) was added in one portion, the solution heated at reflux for 2.5 h, cooled, and poured into a 0° C. solution of 88.6 g of sodium sulfite in 800 mL of water, with vigorous stirring. The aqueous phase was separated, extracted with methylene choride and the combined organics were washed with water and concentrated in vacuo to approximately 200 mL. Toluene (800 mL) was added, the solution was concentrated to a slurry, and the product collected on a filter. Drying under vacuum gave 36.7 g (60%) of a tan powder. 1H NMR (300 MHz, CDCl3) d 8.47 (1H, bs), 7.3-7.1 (3H, m), 7.06 (1H, d, J=8 Hz), 4.68 (1H, t, J=8.7 Hz), 2.97 (1H, m), 2.80-2.60 (3H, m).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. temperaturethe solution heated
  4. temperatureat reflux for 2.5 h
  5. temperaturecooled
  6. customThe aqueous phase was separated
  7. extractionextracted with methylene choride
  8. washthe combined organics were washed with water
  9. concentrationconcentrated in vacuo to approximately 200 mL
  10. additionToluene (800 mL) was added
  11. concentrationthe solution was concentrated to a slurry
  12. customthe product collected on a filter
  13. customDrying under vacuum

출처 및 근거

ORD 기록
ord-d52a91c7557044248d135109a34e5900
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843941

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