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N,N-Dimethylaniline → 2-Benzylthio-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine

HRID 1898802
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HRID 1898802 반응식
CN(C)C1C=CC=CC=1.[CH2:10]([S:17][C:18]1[N:28]=[C:21]2[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25](O)[N:20]2[N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCCCCC.P(Cl)(Cl)([Cl:37])=O>C(OCC)(=O)C>[CH2:10]([S:17][C:18]1[N:28]=[C:21]2[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25]([Cl:37])[N:20]2[N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 949N,N-DimethylanilineHCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 178429177HCID 178429177, 화합물

생성물 1

HCID 190807642-Benzylthio-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

N,N-Dimethylaniline (21,9 g, 0.18 mol) was added slowly to a mixture of 2-benzylthio-5-hydroxyl7-methyl[1,2,4]triazolo[1,5-a]pyridine (44.5 g, 0.164 mol) in 150 mL of phosphorus oxychloride with stirring. The mixture was heated at reflux with stirring for 20 hours. The excess phosphorus oxychloride was then removed by evaporation under reduced pressure. The residue obtained was dissolved in ethyl acetate, washed well with water and quickly concentrated by evaporation under reduced pressure to drive off the excess water. The residue was again dissolved in ethyl acetate and the resulting mixture was filtered with suction through a bed of silica gel. The filtrate was concentrated by evaporation under reduced pressure and the residue obtained was mixed with hexane. The resulting mixture was filtered to recover the solids and dried to obtain the 37.5 g. (79 percent of theory) of the title compound as a tan powder melting at 108°-110° C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. stirringwith stirring for 20 hours
  4. customThe excess phosphorus oxychloride was then removed by evaporation under reduced pressure
  5. customThe residue obtained
  6. washwashed well with water
  7. concentrationquickly concentrated by evaporation under reduced pressure
  8. dissolutionThe residue was again dissolved in ethyl acetate
  9. filtrationthe resulting mixture was filtered with suction through a bed of silica gel
  10. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  11. customthe residue obtained
  12. filtrationThe resulting mixture was filtered
  13. customto recover the solids
  14. customdried
  15. customto obtain the 37.5 g

출처 및 근거

ORD 기록
ord-cb9a8f81ac074c8cb0048f54dc404133
출처 데이터셋
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05571775

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