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

HRID 653572

反応式

HRID 653572 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1f4663c575454f6e849cda5b4abc5106
出典データセット
uspto-grants-1992_07
特許番号
US05127936

関連ノート

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