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Hydrochloric Acid → 9-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-phenyl-6H-pyrimido[2,1-a]isoindol-5-ium hydroxide

HRID 256697
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HRID 256697 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[N:11][CH3:12])=[CH:4][CH:3]=1.Cl.[OH-].[Na+].[C:16](=[C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20])=[O:17].N12CCCC1=NCCC2>C1(C)C=CC=CC=1.O>[OH-:17].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N+:7]3[C:16]([OH:17])=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:19](=[O:20])[N:11]([CH3:12])[C:8]=32)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 107737343-Oxo-2-phenylprop-2-enoyl chlorideHCID 1356242226-Chloro-1-(methylimino)isoindoline

생성물 1

HCID 1784798909-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-phenyl-6H-pyrimido[2,1-a]isoindol-5-ium hydroxide
수율 64.7%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

A mixture of 5.42 g of 6-chloro-1-(methylimino)isoindoline (prepared from the hydrochloride by treatment with 1.5 equivalents of 2N sodium hydroxide solution) and 120 ml of toluene was treated dropwise under argon at 0-50 within 10 minutes with 5.96 g of α-carbonyl-phenylacetyl chloride. The mixture was stirred for 30 minutes, 4.47 g of 1,5-diazabicyclo[4.3.0]non-5-ene in 30 ml of toluene were subsequently added dropwise thereto, the mixture was stirred at 0-50 for a further 90 minutes, then treated with 50 ml of water and the separated crystals were filtered off under suction and washed with 35 ml of methylene chloride and, after drying, there was obtained 3.66 g of 9-chloro1,2-dihydro-4-hydroxy-1-methyl-2-oxo -3-phenyl-6H-pyrimido[2,1-a]isoindole-5-ium hydroxide (internal salt) with a m.p. of 245° (decomposition). This product was recrystallized from N,N-dimethylformamide and then had a m.p. of 288°.

후처리

  1. stirringthe mixture was stirred at 0-50 for a further 90 minutes
  2. filtrationthe separated crystals were filtered off under suction
  3. washwashed with 35 ml of methylene chloride
  4. customafter drying

출처 및 근거

ORD 기록
ord-6668cfc4fe5f40478b199852ca427141
출처 데이터셋
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05258387

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