Water → Ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate

HRID 1413794ノート

反応式

HRID 1413794 の反応式
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][NH:3]1.[H-].[Na+].[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][C:22]=1[Cl:29].O>CN(C)C=O>[Cl:29][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:21]=1[Br:20])[CH2:25][N:3]1[N:4]=[C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]1=[O:1]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 348622Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetateHCID 129473921-Bromo-4-(bromomethyl)-2-chlorobenzene

生成物 1

HCID 20495807Ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate収率 33.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of ethyl 1,2-dihydro-1-oxophthalazin-4-ylacetate (11.5 g.) and sodium hydride (2.7 g.; 50% w/w dispersion in mineral oil) in dimethylformamide (125 ml.) was stirred at 60° C. for 1 hour under nitrogen. The solution obtained was cooled to room temperature and then 4-bromo-3-chlorobenzyl bromide (15.0 g.) was added, and the mixture stirred at 60° C. for 2 hours. After cooling to 25° C. the reaction mixture was poured into water (500 ml.). The aqueous mixture obtained was extracted with ethyl acetate (400 ml.). The extracts were washed with water, dried (MgSO4), and evaporated to give a solid, which was crystallised from propan-2-ol to yield ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate (7.3 g.), m.p. 142°-145° C.

後処理

  1. customThe solution obtained
  2. temperaturewas cooled to room temperature
  3. stirringthe mixture stirred at 60° C. for 2 hours
  4. temperatureAfter cooling to 25° C. the reaction mixture
  5. customThe aqueous mixture obtained
  6. extractionwas extracted with ethyl acetate (400 ml.)
  7. washThe extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a solid, which
  11. customwas crystallised from propan-2-ol

出典と根拠

ORDレコード
ord-e988a28b607843c496bfe61fee60189b
出典データセット
uspto-grants-1981_02
特許番号
US04251528

反応ノート

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