1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22633563, compound

HRID 1532700Notes

Reaction equation

HRID 1532700 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:22]([C:25]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]([CH3:34])[CH3:33])[C:26]=1[NH2:27])([CH3:24])[CH3:23].[Br:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](O)=[O:41]>CN(C=O)C>[Br:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([NH:27][C:26]1[C:25]([CH:22]([CH3:24])[CH3:23])=[CH:31][CH:30]=[CH:29][C:28]=1[CH:32]([CH3:34])[CH3:33])=[O:41]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 163685-Bromovaleric acidHCID 32484DiisopropylanilineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 22633563HCID 22633563, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC (2.87 g, 15 mmols) and HOBt (2.03 g, 15 mmols) were added to a DMF (20 ml) solution of 2,6-diisoproylaniline (1.97 g, 10 mmols) and 5-bromopentanoic acid (2.71 g, 15 mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with ether. The organic layer was washed with water, 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. Then, the residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1), and the resulting crystals were recrystallized from ether-hexane to obtain 1.4 g (41%) of 5-bromo-N-(2,6-diisopropylphenyl)pentanamide as colorless needle-like crystals.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. washThe organic layer was washed with water, 1 N HCl
  3. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThen, the residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1)
  6. customthe resulting crystals were recrystallized from ether-hexane

Sources & evidence

ORD record
ord-60053c8a180244d8a9eb6fc86da8d2f1
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Reaction notes

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