Chloride → 5-Methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazoline-2-carbaldehyde

HRID 1744966ノート

反応式

HRID 1744966 の反応式
CS(C)=O.[Cl-].[CH3:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[N:10]2[N:17]=[C:18]([CH2:20][OH:21])[N:19]=[C:9]2[N:8]=1.C(N(CC)CC)C>ClCCl.O>[CH3:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[N:10]2[N:17]=[C:18]([CH:20]=[O:21])[N:19]=[C:9]2[N:8]=1

参加物

7

反応物 4

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 22224538(5-Methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazolin-2-yl)-methanol

生成物 1

HCID 222245365-Methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazoline-2-carbaldehyde収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒4 回

反応条件

温度
23 °C

実験手順

To a round bottomed flask was loaded l-mi of DMSO and 5 ml dichloromethane. The mixture was cooled to −50˜−60° C. Then a mixture of l-mi oxallyl chloride and 2 ml dichloromethane was injected in into the flask all at once. The mixture was stirred at the same temperature for another 5 minutes. Then 0.218 grams of (5-Methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazolin-2-yl)-methanol in 2 ml dichloromethane was added within 2 minutes. The mixture was stirred at −50˜−60° C. for fifteen minutes and 0.7 ml triethylamine was next added. After another five minutes the reaction media was warmed up to 23° C. and a mixture of 20 ml water and 200 ml dichloromethane was added. The organic layer was dried over magnesium sulfate. Filter off the drying agent and concentrate the filtrate yielded 0.216 grams of product (99%). MS: 217.1(M+H). H-NMR(CDCl3): δ 10.20(s, 1H), 3.23(m, 2H), 2.78 (m, 2H) 2.63 (s, 3H, CH3), 2.00 (m, 4H),

後処理

  1. customTo a round bottomed flask was loaded
  2. temperatureThe mixture was cooled to −50˜−60° C
  3. stirringThe mixture was stirred at −50˜−60° C. for fifteen minutes
  4. customAfter another five minutes the reaction media
  5. additionwas added
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationFilter off the drying agent
  8. concentrationconcentrate the filtrate

出典と根拠

ORDレコード
ord-e3b58cb62d9d4510b0df466a2e46eaf5
出典データセット
uspto-grants-2006_03
特許番号
US07018997B2

反応ノート

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