Dicyclohexylcarbodiimide → 2-(4-Hexylphenyl)-5-(4-allylcarbonyloxyphenyl)-1,3-thiazole

HRID 1587268Notes

Reaction equation

HRID 1587268 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:25]([CH2:27][C:28](O)=[O:29])=[CH2:26].C1(N=C=NC2CCCCC2)CCCCC1>N1(C2C=CN=CC=2)CCCC1.ClCCl>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][C:28]([CH2:27][CH:25]=[CH2:26])=[O:29])=[CH:22][CH:23]=3)=[CH:16][N:17]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 327433-Butenoic acidHCID 233547624-{2-(4-Hexylphenyl)thiazole-5-yl}phenol

Product 1

HCID 197575742-(4-Hexylphenyl)-5-(4-allylcarbonyloxyphenyl)-1,3-thiazoleYield 81.1%

Reagents, catalysts & solvents 2

HCID 755674-PyrrolidinopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

30 ml of dichloromethane was added to 2.0 g (5.93 mM) of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)-1,3-thiazole and 0.52 g (6.16 mM) of vinylacetic acid, followed by stirring at room temperature to the mixture, 1.21 g (5.86 mM) of N,N'-dicyclohexylcarbodiimide (DCC) and 0.02 g of 4-pyrrolidinopyridine were added, followed by stirring for 5 hours at room temperature. The resultant dicyclohexylurea was recovered by filtration, followed by washing with dichloromethane to be added to the filtrate. The resultant dichloromethane solution was condensed into a solid under reduced pressure, followed by purification by silica gel column chromatography (eluent: toluene) and recrystallization from a mixture solvent of ethanol/ethyl acetate to obtain 1.93 g of 2-(4-hexylphenyl)-5-(4-allylcarbonyloxyphenyl)-1,3-thiazole (Yield: 81.1%).

Workup

  1. additionwere added
  2. filtrationThe resultant dicyclohexylurea was recovered by filtration
  3. washby washing with dichloromethane
  4. additionto be added to the filtrate
  5. customcondensed into a solid under reduced pressure
  6. customfollowed by purification by silica gel column chromatography (eluent: toluene) and recrystallization from a mixture solvent of ethanol/ethyl acetate

Sources & evidence

ORD record
ord-37ccadfcfb6f4754b01ae57bef01624a
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

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