Pyridine → Diethyl [(6-acetamido-4-quinazolinylamino)methylene]propanedioate

HRID 354871ノート

反応式

HRID 354871 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClCCl>[C:31]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:33])[CH3:32]

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 20266113Diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioate

生成物 1

HCID 13060488Diethyl [(6-acetamido-4-quinazolinylamino)methylene]propanedioate収率 64.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of diethyl [(6-amino-4-quinazolinylamino)methylene]propanedioate (3.03 g), pyridine (3.63 g) and dichloromethane (93 ml) was ice-cooled. To the mixture was added acetic anhydride (1.88 g). The reaction mixture was stirred for 30 minutes under ice-cooling and then for 2 hours and 15 minutes at ambient temperature. Ice water was added to the mixture. The resultant mixture was extracted with chloroform. The organic layer was washed three times with water and with aqueous solution saturated with sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue, which was purified by a column chromatography on silica gel (developing solvent: chloroform) and recrystallized from chloroform, ethyl acetate and hexane to give crystalline diethyl [(6-acetamido-4-quinazolinylamino)methylene]-propanedioate (2.2 g).

後処理

  1. temperaturecooled
  2. temperaturecooling
  3. waitfor 2 hours
  4. custom15 minutes
  5. customat ambient temperature
  6. extractionThe resultant mixture was extracted with chloroform
  7. washThe organic layer was washed three times with water
  8. dry with materialwith aqueous solution saturated with sodium chloride, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue, which
  11. customwas purified by a column chromatography on silica gel (developing solvent: chloroform)
  12. customrecrystallized from chloroform, ethyl acetate and hexane

出典と根拠

ORDレコード
ord-8279d0b0c6bc403baf9e6d077860c57c
出典データセット
uspto-grants-1983_03
特許番号
US04377580

反応ノート

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