Dicyclohexylcarbodiimide → 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-octylthiazole

HRID 2121301Notes

Reaction equation

HRID 2121301 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][N:27]=2)=[CH:19][CH:18]=1.[C:36](O)(=[O:42])/[CH:37]=[CH:38]/[CH2:39][CH2:40][CH3:41]>CN(C)C1C=CN=CC=1.ClCCl>[C:36]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[S:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][N:27]=2)=[CH:21][CH:22]=1)(=[O:42])/[CH:37]=[CH:38]/[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 52827072-Hexenoic acid, (2E)-HCID 1358448422-(4-Hydroxyphenyl)-5-octylthiazole

Product 1

HCID 234320602-(4-[(E)-hex-2-enoyloxy]phenyl)-5-octylthiazoleYield 45%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dicyclohexylcarbodiimide (0.2 g) is added to a solution of 2-(4-hydroxyphenyl)-5-octylthiazole (0.25 g), (E)-hex-2-enoic acid, (0.1 g) 4-(dimethylamino)pyridine (0.05 g) and dichloromethane (20 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture is stirred overnight at room temperature, filtered to remove inorganic material and the filtrate evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (9/1 v/v) as eluent and recrystallisation from hexane to yield 0.15 g of 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-octylthiazole.

Workup

  1. filtrationfiltered
  2. customto remove inorganic material
  3. customthe filtrate evaporated down
  4. customThe residue is purified by column chromatography on silica gel
  5. customrecrystallisation from hexane

Sources & evidence

ORD record
ord-a84420e1b3934a5d9c3dd9d84675595e
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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