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

HRID 327571Notes

Reaction equation

HRID 327571 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-66c51b97192543d78bfbca8972a5291c
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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