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Sodium Methoxide → 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one

HRID 703155
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HRID 703155 반응식
[CH3:1][C:2]1([CH3:29])[C:13]2[C:5](=[CH:6][C:7]3[NH:8][C:9]([S:14][CH2:15][C:16]4[C:21]([CH3:22])=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][N:17]=4)=[N:10][C:11]=3[CH:12]=2)[C:4]([CH3:27])([CH3:26])[C:3]1=[O:28].[CH3:30][O-:31].[Na+]>CO>[CH3:30][O:31][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:15][S:14][C:9]2[NH:8][C:7]3[CH:6]=[C:5]4[C:13](=[CH:12][C:11]=3[N:10]=2)[C:2]([CH3:29])([CH3:1])[C:3](=[O:28])[C:4]4([CH3:27])[CH3:26])[C:21]=1[CH3:22]
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참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 221514395,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-4-nitro-2-pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one

생성물 1

HCID 98654732-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 4.4 g of 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-4-nitro-2-pyridyl)met hyl]thio]indeno[5,6-d]imidazol-6(lH)-one in 100 ml of absolute methanol was treated with 3 g of sodium methylate, whereupon the mixture was boiled at reflux for 18 hours under argon. After concentrating the reaction mixture in vacuo the residue was treated with methylene chloride whereupon the mixture was buffered by means of glacial acetic acid; the methylene chloride phase was extracted several times with a sodium bicarbonate solution, dried and evaporated. By recrystallisation from ethyl acetate there was obtained 5,7-dihydro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d ]imidazol-6(lH)-one of melting point 222-226°.

후처리

  1. temperatureat reflux for 18 hours under argon
  2. concentrationAfter concentrating the reaction mixture in vacuo the residue
  3. additionwas treated with methylene chloride whereupon the mixture
  4. extractionthe methylene chloride phase was extracted several times with a sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customBy recrystallisation from ethyl acetate

출처 및 근거

ORD 기록
ord-922ccdb4b814429cafddab210f39e175
출처 데이터셋
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04981861

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