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Bromoform → 2-Bromo-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1054981
ノート
印刷プレビュー

反応式

HRID 1054981 の反応式
[CH3:1][C:2]1[N:7]2[N:8]=[C:9](N)[N:10]=[C:6]2[C:5]([CH3:12])=[N:4][CH:3]=1.N([O-])=O.[Na+].C(Br)(Br)[Br:18].ClC(Cl)C(O)=O>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Al].O>[Br:18][C:9]1[N:10]=[C:6]2[C:5]([CH3:12])=[N:4][CH:3]=[C:2]([CH3:1])[N:7]2[N:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 5558BromoformHCID 6597Dichloroacetic AcidHCID 23668193Sodium NitriteHCID 900260875,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine

生成物 1

HCID 900257482-Bromo-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine収率 143.7%

試薬・触媒・溶媒 3

HCID 165294
Benzyltriethylammonium bromide
触媒
HCID 962Water溶媒
HCID 5359268Aluminum溶媒

反応条件

温度
25 °C

実験手順

A mixture of 5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine (2.4 g, 14.71 mmol), sodium nitrite (10.15 g, 147.08 mmol) and benzyltriethylammonium bromide (8 g, 29.42 mmol) in bromoform (76.2 ml, 872.17 mmol) was stirred at 25° C. for 30 minutes. To this mixture was then added dichloroacetic acid (2.43 ml, 29.42 mmol) and the reaction mixture was stirred at 25° C. for further 20 hours. (The reaction flask was wrapped in aluminum foil to protect the mixture from light). Water (100 ml) was added to the reaction mixture, which was then stirred for 30 minutes at 25° C., and finally extracted 4 times with dichloromethane. The combined organic layers were washed twice with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated. The crude material thus obtained was purified by silica gel column chromatography using hexane ethyl acetate 20% as eluent affording 2-bromo-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (4.8 g, 74.72%) as an off white solid. MS: m/z=227 (M+H+)

後処理

  1. stirringwas then stirred for 30 minutes at 25° C.
  2. extractionfinally extracted 4 times with dichloromethane
  3. washThe combined organic layers were washed twice with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material thus obtained
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-c67e631293d74f34a923ee368255f971
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394311B2

反応ノート

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