Pyridine → HCID 57747433、化合物

HRID 386621ノート

反応式

HRID 386621 の反応式
[Br:1][C:2]1[CH:19]=[C:18]([CH3:20])[C:5]([O:6][C:7]2[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([CH3:16])[N:10]=[C:9](Cl)[N:8]=2)=[C:4]([CH3:21])[CH:3]=1.[NH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.N1C=CC=CC=1>C1COCC1.CO>[Br:1][C:2]1[CH:19]=[C:18]([CH3:20])[C:5]([O:6][C:7]2[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([CH3:16])[N:10]=[C:9]([NH:22][C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=3)[N:8]=2)=[C:4]([CH3:21])[CH:3]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 133964-AminobenzonitrileHCID 57747430HCID 57747430、化合物

生成物 1

HCID 57747433HCID 57747433、化合物収率 84.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-(4-bromo-2,6-dimethylphenoxy)-2-chloro-6-methyl-5-nitropyrimidine (22.0 g, 59.3 mmol), 4-aminobenzonitrile (7.7 g. 65.2 mmol) and pyridine (4.8 ml, 59.3 mmol) in THF (300 ml) was heated to 80° C. for 10 hours. The reaction mixture was dissolved in methanol, washed with brine and extracted with ethyl acetate. The organic layer was washed twice with brine, dried over MgSO4 and concentrated to dryness. The solid was washed with a mixture of hexane:ethyl acetate (80:20) before filtration. After filtration, the solid was washed again with methanol. The filtrate was concentrated again until dryness. The second round of precipitation was collected following the same procedure. The operation was repeated until total product was recovered. The combined solids were recrystallized from acetone to obtain the title compound (22.72 g, 50 mmol, 84%). 1H NMR (CDCl3, 400 MHz) δ 2.14 (s, 6H), 2.60 (s, 3H), 7.22 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.9, 2H), 7.27 (s, 2H), 12.75 (bs, 1H).

後処理

  1. washwashed with brine
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed twice with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. washThe solid was washed with a mixture of hexane:ethyl acetate (80:20) before filtration
  7. filtrationAfter filtration
  8. washthe solid was washed again with methanol
  9. concentrationThe filtrate was concentrated again until dryness
  10. customThe second round of precipitation
  11. customwas collected
  12. customwas recovered
  13. customThe combined solids were recrystallized from acetone

出典と根拠

ORDレコード
ord-0173e971f35f423cbb38de0b9cc94395
出典データセット
uspto-grants-2013_02
特許番号
US08372852B2

反応ノート

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