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

HRID 638884노트

반응식

HRID 638884 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매4회

반응 조건

온도
23 °C

실험 절차

To a round bottomed flask was loaded 1 ml of DMSO and 5 ml dichloromethane. The mixture was cooled to −50˜−60° C. Then a mixture of 1 ml 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),

후처리

  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

출처 및 근거

ORD 기록
ord-aff2b75073144d38aa736e3c6325affa
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691842B2

반응 노트

불러오는 중…