Dicyclohexylcarbodiimide → 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole

HRID 2121304Notes

Reaction equation

HRID 2121304 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][CH3:32])=[N:26][N:27]=2)=[CH:19][CH:18]=1.[C:33](O)(=[O:39])/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH3:38]>CN(C)C1C=CN=CC=1.ClCCl>[C:33]([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][CH3:32])=[N:26][N:27]=2)=[CH:21][CH:22]=1)(=[O:39])/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 52827072-Hexenoic acid, (2E)-HCID 1358448412-(4-Hydroxyphenyl)-5-pentyl-1,3,4-thiadiazole

Product 1

HCID 234321882-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dicyclohexylcarbodiimide (0.2 g) is added to a solution of 2-(4-hydroxyphenyl)-5-pentyl-1,3,4-thiadiazole [Mol. Cryst. Liq. Cryst., (1990) Vol., 191, pp 223] (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 hexanelethyl acetate (9/1 v/v) as eluent and recrystallisation from hexane to yield 0.17 g of 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole.

Workup

  1. customat 0° C.
  2. filtrationfiltered
  3. customto remove inorganic material
  4. customthe filtrate evaporated down
  5. customThe residue is purified by column chromatography on silica gel using hexanelethyl acetate (9/1 v/v) as eluent
  6. customrecrystallisation from hexane

Sources & evidence

ORD record
ord-3ab43c7b9f8f47bc8d2dc3a4415e9c87
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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