2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-n-Butyl-5-methoxy-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one

HRID 889826노트

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HRID 889826 반응식
[CH2:1]([N:5]1[C:10](=[O:11])[NH:9][CH2:8][C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[N:6]1)[CH2:2][CH2:3][CH3:4].C(C1C(=O)C(Cl)=C(Cl)[C:23](=[O:24])C=1C#N)#N>C(OCC)(=O)C>[CH2:1]([N:5]1[C:10](=[O:11])[NH:9][CH:8]([O:24][CH3:23])[C:7]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[N:6]1)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 691180472-n-Butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one

생성물 1

HCID 691182622-n-Butyl-5-methoxy-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

2-n-Butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one (2.16 g, 8.13 mmol), and DDQ (1.94 g, 8.5 mmol in 80 mL of ethyl acetate were stirred at room temperature overnight, then refluxed for 3 hours. The reaction mixture was cooled, washed twice with aqueous potassium carbonate solution, washed with brine, dried over magnesium sulfate and stripped. The product was dissolved in 15 mL of ethyl acetate and 15 mL of methanol. Alumina (7 g) was added, and the slurry was stirred for 3 hours at room temperature. The slurry was filtered, and the filtrate was stripped. The product was chromatographed on an alumina column to give 0.97 g of of 2-n-butyl-5-methoxy-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one (Compound 3).

후처리

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed twice with aqueous potassium carbonate solution
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. dissolutionThe product was dissolved in 15 mL of ethyl acetate
  7. additionAlumina (7 g) was added
  8. filtrationThe slurry was filtered
  9. customThe product was chromatographed on an alumina column

출처 및 근거

ORD 기록
ord-ffe80216a660446ba5a597ab08c2e7f3
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995157B2

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