4-Chlorothiobenzamide → 3-[2-(4-Chloro-phenyl)thiazol-4-yl]bicyclo[3.2.1]octane-2,4-dione

HRID 45910Notes

Reaction equation

HRID 45910 reaction equation
Cl[CH2:2][C:3]([CH:5]1[C:11](=[O:12])[CH:10]2[CH2:13][CH:7]([CH2:8][CH2:9]2)[C:6]1=[O:14])=O.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[S:21])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]2[S:21][CH:2]=[C:3]([CH:5]3[C:11](=[O:12])[CH:10]4[CH2:13][CH:7]([CH2:8][CH2:9]4)[C:6]3=[O:14])[N:22]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 27348264-ChlorothiobenzamideHCID 866619563-(2-Chloro-acetyl)bicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 667427193-[2-(4-Chloro-phenyl)thiazol-4-yl]bicyclo[3.2.1]octane-2,4-dioneYield 53.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(2-chloro-acetyl)bicyclo[3.2.1]octane-2,4-dione (3.16 g, 14.7 mmol) and 4-chloro-thiobenzamide (2.53 g, 14.7 mmol) are mixed together in toluene (50 ml) and heated under reflux overnight. Therefore, the reaction mixture was evaporated to a black gum and the gum was absorbed onto silica and purified by flash chromatography eluting with a gradient of hexane/ethyl acetate to give 3-[2-(4-chloro-phenyl)thiazol-4-yl]bicyclo[3.2.1]octane-2,4-dione (2.6 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. customTherefore, the reaction mixture was evaporated to a black gum
  4. customthe gum was absorbed onto silica
  5. custompurified by flash chromatography
  6. washeluting with a gradient of hexane/ethyl acetate

Sources & evidence

ORD record
ord-f5a8391c359a43e2abd10f31d51a2ced
Source dataset
uspto-grants-2013_09
Patent number
US08541594B2

Reaction notes

Loading…