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

HRID 1074549

반응식

HRID 1074549 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1bee9c7e61074308af24011cd4849793
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04393062

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