Acrolein → 3-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde

HRID 1266978ノート

反応式

HRID 1266978 の反応式
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=[O:11])=[O:8].[CH:13]([CH:15]=[CH2:16])=[O:14]>CO.C(OCC)(=O)C.O>[O:11]=[C:10]1[N:9]([CH2:16][CH2:15][CH:13]=[O:14])[C:7](=[O:8])[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[NH:12]1

参加物

6

反応物 2

HCID 7847AcroleinHCID 64048Quinazolinedione

生成物 1

HCID 185451873-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde収率 59.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒3 回HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

Benzoylene urea (4.0 9, 24.7 mmol), Triton B (40 wt % in methanol) (11.0 mL, 24.7 mmol), water (80 mL) and methanol (400 mL) were combined at ambient temperature and stirred vigorously for 15 minutes. (until all the solids had gone into solution). To this colorless solution, acrolein (1.7 mL, 24.7 mmol) in methanol (20 mL) was added dropwise over 5 minutes. to give a yellow solution. The reaction was then heated to 55° C. and stirred for 2 hours. and then at room temperature for approximately 16 hours. The yellow solution was concentrated to give a yellow oil which was taken up in ethyl acetate (25 mL) and water (50 mL). The aqueous layer was extracted again with ethyl acetate (25 mL). The organic layers were combined, washed with 1N HCl (20 mL), water (20 mL), saturated sodium bicarbonate solution (20 mL) and brine (20 mL), the organic layer was dried over magnesium sulfate and concentrated to give 3-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde as a yellow foam (3.2 g, 59%) which was used without further purification. The NMR data showed a purity of ˜70%. NMR CDCl3 δ9.85 (s, 1H), 8.10-8.06 (m, 1H), 7.63-7.57 (m, 1H), 7.24-7.19 (m, 1H), 7.13-7.07 (m, 1H), 4.44-4.40 (m, 2H), 2.85 (dt, 2H, J1,2=2 Hz, J1,3=7 Hz); MS=219 (p+1).

後処理

  1. customwere combined at ambient temperature
  2. customto give a yellow solution
  3. stirringstirred for 2 hours
  4. waitand then at room temperature for approximately 16 hours
  5. concentrationThe yellow solution was concentrated
  6. customto give a yellow oil which
  7. extractionThe aqueous layer was extracted again with ethyl acetate (25 mL)
  8. washwashed with 1N HCl (20 mL), water (20 mL), saturated sodium bicarbonate solution (20 mL) and brine (20 mL)
  9. dry with materialthe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-073276b0e1bb40b8abeee2d365ecd3f8
出典データセット
uspto-grants-2003_04
特許番号
US06552015B2

反応ノート

読み込み中…