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Dimethylformamide → Diethyl [(6-pivalamido-4-quinazolinylamino)methylene]propanedioate

HRID 354872
ノート
印刷プレビュー

反応式

HRID 354872 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])([O-])=O.CN(C)[CH:29]=[O:30]>[Pd].[H][H]>[C:29]([NH:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:30])[C:6]([CH3:11])([CH3:7])[CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 13060485Diethyl[(6-nitro-4-quinazolinylamino)methylene]propanedioate

生成物 1

HCID 13060496Diethyl [(6-pivalamido-4-quinazolinylamino)methylene]propanedioate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 178418361HCID 178418361、化合物溶媒2 回

実験手順

A suspension of diethyl [(6-nitro-4-quinazolinylamino)methylene]propanedioate (10.8 g) in N,N-dimethylformamide (380 ml) was shaken with 10% palladium on carbon (3.6 g) in hydrogen atmosphere at ambient temperature until hydrogen gas (2030 ml) was absorbed. The catalyst was removed by filtration and washed with a small volume of N,N-dimethylformamide. To the combined filtrate and washings was added pyridine (17 ml) and the mixture was cooled over an ice-bath. To the solution was added dropwise pivalic chloride (6.33 g) for 20 minutes and then the reaction mixture was stirred for 2 hours and 40 minutes at ambient temperature. To the resultant mixture was added ice-water under stirring and then the mixture was concentrated under reduced pressure. To the residue was added chloroform and then the mixture was washed with an aqueous solution saturated with sodium bicarbonate and with water. Insoluble materials were removed by filtration from the chloroform layer. The filtrate was washed with aqueous solution saturated with sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant oil was subjected to a chromatography using silica gel (developing solvent: dichloromethane) to give the first Fraction A and the second Fraction B. The Fraction A was concentrated under reduced pressure to give crystalline diethyl [(6-pivalamido-4-quinazolinylamino)methylene]propanedioate (4.6 g). Further, Fraction B was concentrated under reduced pressure to give a solid (3.6 g), which was suspended in methanol. Insoluble materials were separated by filtration and recrystallized from ethyl acetate to give crystalline diethyl [(6-formamido-4-quinazolinylamino)methylene]propanedioate (0.58 g).

後処理

  1. customwas absorbed
  2. customThe catalyst was removed by filtration
  3. washwashed with a small volume of N,N-dimethylformamide
  4. additionTo the combined filtrate and washings was added pyridine (17 ml)
  5. temperaturethe mixture was cooled over an ice-bath
  6. additionTo the solution was added dropwise pivalic chloride (6.33 g) for 20 minutes
  7. additionTo the resultant mixture was added ice-water
  8. stirringunder stirring
  9. concentrationthe mixture was concentrated under reduced pressure
  10. additionTo the residue was added chloroform
  11. washthe mixture was washed with an aqueous solution saturated with sodium bicarbonate and with water
  12. customInsoluble materials were removed by filtration from the chloroform layer
  13. washThe filtrate was washed with aqueous solution saturated with sodium chloride
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customto give the first Fraction A
  17. concentrationThe Fraction A was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-aedfc577fc2b47daaa8e62db0c9add50
出典データセット
uspto-grants-1983_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04377580

反応ノート

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