Benzimidazole → HCID 22731922、化合物

HRID 2083902ノート

反応式

HRID 2083902 の反応式
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.[Br:12][C:13]1[C:14](Cl)=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1.C(OCC)(=O)C>CN(C=O)C.O>[Br:12][C:13]1[C:14]([N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1

参加物

7

反応物 4

HCID 5798BenzimidazoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2899735-Bromo-2,4-dichloropyrimidine

生成物 1

HCID 22731922HCID 22731922、化合物収率 64.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

Sodium hydride (60% dispersion in oil; 110 mg, 2.75 mmol) was added to a solution of benzimidazole (295 mg, 2.5 mmol) in DMF (6 ml) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then added dropwise to a cold (0° C.) solution of 5-bromo-2,4-dichloropyrimidine (712 mg, 3.14 mmol) in DMF (6 ml). The mixture was stirred for at 0° C. for 2 hours and then ethyl acetate (20 ml) and water (20 ml) were added. The organic phase was separated and dried and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 20% ethyl acetate/DCM, to give the product as a white solid (500 mg, 52%). NMR: 7.4 (m, 2H), 7.8 (m, 2H), 8.8 (s, 1H), 9.3 (s, 1H); MS (MH+): 309, 311.

後処理

  1. stirringThe mixture was stirred for at 0° C. for 2 hours
  2. customThe organic phase was separated
  3. customdried
  4. customvolatile material was removed by evaporation
  5. customThe residue was purified by column chromatography
  6. washeluting with 20% ethyl acetate/DCM

出典と根拠

ORDレコード
ord-bbb9f9b599e94bc3b7034752dc086bb6
出典データセット
uspto-grants-2004_04
特許番号
US06716831B1

反応ノート

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