Dicyclohexylcarbodiimide → 1-(19-Carboxynonadecanoyl)benzotriazole

HRID 1075652

Reaction equation

HRID 1075652 reaction equation
[C:1]([OH:24])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].C1(N=C=NC2CCCCC2)CCCCC1.[NH:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[N:41]1.Cl.CN(C1C=CC=CN=1)C>O1CCCC1>[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([N:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[N:42]=[N:41]1)=[O:24])([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 75502Eicosanedioic AcidHCID 22461520Dimethylaminopyridine hydrochlorideHCID 178418385HCID 178418385, compound

Product 1

HCID 536938761-(19-Carboxynonadecanoyl)benzotriazoleYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of eicosanedioic acid (3.43 g, 10.0 mmol), dicyclohexylcarbodimide (2.06 g, 10.0 mmol), benzotriazole (1.19 g, 10.0 mmol) and dimethylamino-pyridine hydrochloride in anhydrous tetrahydrofuran (200 ml) was stirred for two days at room temperature. The resulting suspension was filtered, and the filtrate evaporated to dryness under reduced pressure. The residue was suspended in dichloromethane (100 ml), and undissolved material was isolated by filtration. The dried filter cake (2.0 g) was recrystallised from acetone (200 ml) yielding 0.70 g (16%) of white crystalline 1-(19-carboxynonadecanoyl)benzotriazole, melting at 111.9° C. (DSC peak value).

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. customundissolved material was isolated by filtration
  4. filtrationThe dried filter cake (2.0 g)
  5. customwas recrystallised from acetone (200 ml)

Sources & evidence

ORD record
ord-2300098609134e2a9f544a32eecd9e99
Source dataset
uspto-grants-1999_05
Patent number
US05905140

Linked notes

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