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

HRID 1456630

反応式

HRID 1456630 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
30 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d52a91c7557044248d135109a34e5900
出典データセット
uspto-grants-1998_12
特許番号
US05843941

関連ノート

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