Water → N-benzyl-N-(4-bromo-3-oxobutyl)-2-nitrobenzenesulfonamide

HRID 526723ノート

反応式

HRID 526723 の反応式
[CH2:1]([N:8]([CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:26]Br.O>CO>[CH2:1]([N:8]([CH2:21][CH2:22][C:23](=[O:25])[CH2:24][Br:26])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 962WaterHCID 24408Bromine2 回HCID 71152136N-benzyl-2-nitro-N-(3-oxobutyl)benzenesulfonamide2 回

生成物 1

HCID 71502814N-benzyl-N-(4-bromo-3-oxobutyl)-2-nitrobenzenesulfonamide収率 53.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
30 °C

実験手順

To a solution of N-benzyl-2-nitro-N-(3-oxobutyl)benzenesulfonamide (compound F, 30 g, 83 mmol) in methanol (300 ml) was added bromine (4.69 ml, 91 mmol) in one portion at 20-25° C. Stirred for 20 hours (no bromine colour), water (20 ml) added, heated to reflux for 30 min, diluted with MeOH (100 ml). The solution was cooled to 30° C. with stirring, seeded with compound G, stirred at 25-30° C. for 5 min (crystallisation occurred), cooled to 15° C., aged for 1 hour. Crystals collected, washed with 2×15 ml of MeOH (20-25° C.), dried on air to give N-benzyl-N-(4-bromo-3-oxobutyl)-2-nitrobenzenesulfonamide (19.4 g, 44.0 mmol, 53.1% yield).

後処理

  1. additionadded
  2. temperatureheated
  3. temperatureto reflux for 30 min
  4. stirringstirred at 25-30° C. for 5 min
  5. custom(crystallisation occurred)
  6. temperaturecooled to 15° C.
  7. customCrystals collected
  8. washwashed with 2×15 ml of MeOH (20-25° C.)
  9. customdried on air

出典と根拠

ORDレコード
ord-370cf6944fec4aaea716719aca1f5a39
出典データセット
uspto-grants-2016_05
特許番号
US09346751B2

反応ノート

読み込み中…