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3-Nitrobenzaldehyde → (E)-2-cyclobutyl-4-[2-(3-nitrophenyl)ethenyl]thiazole

HRID 1609333
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HRID 1609333 반응식
[Cl-].[CH:2]1([C:6]2[S:7][CH:8]=[C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:10]=2)[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[N+:33]([C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=O)([O-:35])=[O:34]>O1CCCC1.C(Cl)Cl>[CH:2]1([C:6]2[S:7][CH:8]=[C:9](/[CH:11]=[CH:39]/[C:38]3[CH:41]=[CH:42][CH:43]=[C:36]([N+:33]([O-:35])=[O:34])[CH:37]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 74493-NitrobenzaldehydeHCID 24758Sodium hydrideHCID 20084325[(2-Cyclobutyl-4-thiazolyl)methyl]triphenylphosphonium chloride

생성물 1

HCID 20084352(E)-2-cyclobutyl-4-[2-(3-nitrophenyl)ethenyl]thiazole수율 70.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

A slurry of 1.8 g of [(2-cyclobutyl-4-thiazolyl)methyl]triphenylphosphonium chloride, in 80 ml of tetrahydrofuran was sealed under a positive argon atmosphere and the mixture cooled with an ice bath. Sodium hydride (0.2 g; 50% oil dispersion) was added and stirring and cooling continued for 30 min afterwhich 0.6 g of 3-nitrobenzaldehyde was added. The cooling bath was removed and the mixture was stirred at room temperature for 1 hr. The mixture was then filtered, condensed in vacuo and the residual materials taken up in 100 ml of methylene chloride. This solution was then washed with water, dried (MgSO4) and condensed in vacuo to yield 0.8 g of (E)-2-cyclobutyl-4-[2-(3-nitrophenyl)ethenyl]thiazole; m.p. 112°-115° C.

후처리

  1. temperaturethe mixture cooled with an ice bath
  2. temperaturecooling
  3. additionwas added
  4. customThe cooling bath was removed
  5. stirringthe mixture was stirred at room temperature for 1 hr
  6. filtrationThe mixture was then filtered
  7. customcondensed in vacuo
  8. washThis solution was then washed with water
  9. customdried
  10. custom(MgSO4) and condensed in vacuo

출처 및 근거

ORD 기록
ord-ba6f8c48fdfa46629b0af1a45b44cbdc
출처 데이터셋
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05399702

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