Phthalimide → 2H-Isoindole-2-carbonitrile, 1,3-dihydro-1,3-dioxo-

HRID 1587038ノート

反応式

HRID 1587038 の反応式
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[N:12]#[C:13]Br.C(N(CC)CC)C>CC(C)=O>[O:6]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:11])[N:5]1[C:13]#[N:12]

参加物

5

反応物 3

HCID 6809PhthalimideHCID 8471TriethylamineHCID 10476Cyanogen Bromide

生成物 1

HCID 109974912H-Isoindole-2-carbonitrile, 1,3-dihydro-1,3-dioxo-収率 77%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a 25 mL round-bottomed flask was added phthalimide (1.47 g, 10.0 mmol), cyanogen bromide (1.27 g, 12.0 mmol), and 10 mL of reagent grade acetone. The resulting mixture was cooled using an ice/salt bath while triethylamine (1.8 mL, 12.8 mmol) was added dropwise over a 2 minute period. After 15 minutes, the mixture was transferred to a separatory funnel and partitioned between ethyl acetate and water. The organic phase was washed with water, saturated brine, dried (MgSO4), and filtered. The solution was decolorized with activated charcoal, and concentrated to give a brown solid. This material was recrystallized from ethyl acetate to give 1.32 g (77%) of a brown crystalline solid, mp 189°-191° C. (reported in Zh. Org. Khim. 1977, 13, 968 as 190° C.): IR (nujol) 2258 (nitrile), 1755 (carbonyl) cm-1 ; 1H NMR (200 MHz, DMSO) δ 8.05-8.15 (m, 4); 13C NMR (50 MHz, DMSO) δ 162.61, 136.35, 130.76, 125.03, 102.86.

後処理

  1. temperatureThe resulting mixture was cooled
  2. additionwas added dropwise over a 2 minute period
  3. customthe mixture was transferred to a separatory funnel
  4. custompartitioned between ethyl acetate and water
  5. washThe organic phase was washed with water, saturated brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown solid
  10. customThis material was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-1ff90f27b47b472f87998d02b6c6fc92
出典データセット
uspto-grants-1993_06
特許番号
US05216173

反応ノート

読み込み中…