Dimethylformamide → 3-Chloro-6-phenyl-1,2,4-triazine

HRID 1099031노트

반응식

HRID 1099031 반응식
[C:1]1([C:7]2[CH:8]=[N:9][C:10](=O)[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.P(Cl)(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][C:10]1[N:11]=[N:12][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][N:9]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 112637836-Phenyl-1,2,4-triazin-3(2H)-one

생성물 1

HCID 110306323-Chloro-6-phenyl-1,2,4-triazine수율 81.4%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 6-phenyl-1,2,4-triazin-3(2H)-one (2.45 g, 0.0141 mol) and DMF (0.5 mL) in phosphoryl chloride (20.0 mL, 0.214 mol) and chloroform (20.0 mL) was heated under reflux overnight. After cooling, the volatiles were removed under reduced pressure. The residue was dissolved in DCM (60 mL) and was poured into ice with stirring. The mixture was neutralized with NaOH (1N), and filtered through a pad of celite to remove a small amount of insoluble residue. The organic layer was separated. The aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was flash chromatographed on a silica gel column to give the desired product (2.20 g, 81.1%). Analytical LCMS: (M+H)+=192.1/194.1.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customthe volatiles were removed under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (60 mL)
  6. additionwas poured into ice
  7. filtrationfiltered through a pad of celite
  8. customto remove a small amount of insoluble residue
  9. customThe organic layer was separated
  10. extractionThe aqueous layer was extracted with DCM (3×20 mL)
  11. dry with materialThe combined organic layers were dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customchromatographed on a silica gel column

출처 및 근거

ORD 기록
ord-cf4d3b85ec3241148dde58a2bb7e9bb3
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143251B2

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