Pyridine → HCID 57747433, 화합물

HRID 222065노트

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HRID 222065 반응식
[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

참가 물질

6

반응물 3

HCID 1049PyridineHCID 133964-AminobenzonitrileHCID 57747430HCID 57747430, 화합물

생성물 1

HCID 57747433HCID 57747433, 화합물수율 84.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a159a2d1da62487097e8bf879d3909d8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207178B2

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