Dichloromethane → 2-Chloro-5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine

HRID 653572

반응식

HRID 653572 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]2[N:14]=[C:15](N)[N:16]=[C:4]2[N:3]=1.N([O-])=O.[Na+].C(OCC)(=O)C.C(Cl)[Cl:29]>Cl.O.C(Cl)Cl.C(OCC)(=O)C>[Cl:29][C:15]1[N:16]=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]2[N:14]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 9757135-Methyl-7-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-2-amineHCID 23668193Sodium Nitrite

생성물 1

HCID 198890512-Chloro-5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매2회HCID 21226138Dichloromethane ethylacetate용매

실험 절차

To 2.0 g (8.9 mmol) of 5-methyl-7-phenyl-1,2,4triazolo[1,5-a]pyrimidin-2-amine stirring in 25 ml of concentrated hydrochloric acid, 1.2 g (17.4 mmol) of sodium nitrite dissolved in 4.0 ml of water was added dropwise at ambient temperature. After the addition, the reaction suspension was warmed at about 60° for 15 minutes followed by stirring another 10 minutes without heat. Ethyl acetate (150 ml) and excess water were added. The ethyl acetate layer was separated whereby a certain amount of insoluble material present was ignored and the extract washed with water (2X), saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid residue. Silica gel column chromatography (methylene chloride followed by 10:1 methylene chloride/ethyl acetate) afforded the title compound, m.p. 179°-181° C.

후처리

  1. additionwas added dropwise at ambient temperature
  2. additionAfter the addition
  3. temperaturethe reaction suspension was warmed at about 60° for 15 minutes
  4. temperaturewithout heat
  5. customThe ethyl acetate layer was separated whereby a certain amount of insoluble material present
  6. washthe extract washed with water (2X), saturated sodium bicarbonate, brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a solid residue

출처 및 근거

ORD 기록
ord-1f4663c575454f6e849cda5b4abc5106
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05127936

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