Acetone → HCID 15707394、化合物

HRID 1587040

反応式

HRID 1587040 の反応式
[C@@H:1]12[C:9](=[O:10])[NH:8][C:7](=[O:11])[C@@H:2]1[CH2:3][CH:4]=[CH:5][CH2:6]2.[N:12]#[C:13]Br.CC(C)=O.C(N(CC)CC)C>C(OCC)(=O)C>[C:13]([N:8]1[C:7](=[O:11])[C@@H:2]2[CH2:3][CH:4]=[CH:5][CH2:6][C@@H:1]2[C:9]1=[O:10])#[N:12]

参加物

6

反応物 4

HCID 180AcetoneHCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 92888cis-1,2,3,6-Tetrahydrophthalimide

生成物 1

HCID 15707394HCID 15707394、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Using a 250 mL round-bottomed flask equipped with a magnetic stir bar and an ice/salt bath, a suspension of cis-4-cyclohexene-1,2-dicarboximide (15.1 g, 100 mmol), cyanogen bromide (11.7 g, 110 mmol), and 100 mL of acetone was cooled to 0° C. Triethylamine (16.0 mL, 115 mmol) was added via syringe over a 12 minute period. The resulting peach slurry was allowed to stir for 15 minutes. The mixture was diluted with ethyl acetate and filtered to remove solid triethylamine hydrobromide. The filter cake was rinsed with ethyl acetate and the filtrate was concentrated using a rotary evaporator. The crude paste was partitioned between water and a 2:1 mixture of ethyl acetate/hexanes. The organic phase was washed with brine, dried (MgSO4), and concentrated to give a light brown solid. The crude product was purified by recrystallization using ethyl acetate/pet ether or ethyl acetate/hexanes to afford 11.5 g (65%) of a glossy off white solid, mp 136°-138° C.: IR (nujol) 2256 (nitrile), 1749 (carbonyl) cm-1 ; 1H NMR (200 MHz, CDCl3) δ 2.30 (ddd, 2, J=15, 4.4, 2.75 Hz), 2.64 (ddd, 2, J=15, 3.8, 2.75 Hz), 3.35 (dd, 2, J=3.5, 2.75 Hz), 5.98 (ddd, 2, J= 3.9, 1.7, 1.5 Hz); 13C NMR (50 MHz, CDCl3) δ 173.48, 127.52, 100.72, 40.08, 23.26; GC/MS m/e (relative intensity) 176 (29.5), 147 (11.1), 107 (20.0), 105 (23.3), 80 (44.0), 79 (100), 78 (35.1).

後処理

  1. customequipped with a magnetic stir bar and an ice/salt bath
  2. filtrationfiltered
  3. customto remove solid triethylamine hydrobromide
  4. washThe filter cake was rinsed with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customa rotary evaporator
  7. customThe crude paste was partitioned between water
  8. additiona 2:1 mixture of ethyl acetate/hexanes
  9. washThe organic phase was washed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customto give a light brown solid
  13. customThe crude product was purified by recrystallization
  14. customto afford 11.5 g (65%) of a glossy off white solid, mp 136°-138° C.

出典と根拠

ORDレコード
ord-1b353516304f4848a8db7c49eb087d8d
出典データセット
uspto-grants-1993_06
特許番号
US05216173

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