Pyridine → HCID 22177449, compound

HRID 1797347Notes

Reaction equation

HRID 1797347 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[N+:14]([C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[C:20](Cl)=[O:21])([O-:16])=[O:15].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[N+:14]([C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[C:20]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[O:21])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 7416311-Bromo-1-undecanol

Product 1

HCID 22177449HCID 22177449, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

11.4 g (45.4 mmol) 11-bromo-1-undecanol, 11.0 g (47.7 mmol) 3,5-dinitrobenzoyl chloride, 54 mg 4-dimethylaminopyridine were dissolved in 94 ml dichloromethane. The solution was subsequently cooled to 0° C. and then 18.3 ml (227 mmol) pyridine was added dropwise, in the course of 25 minutes. After 4.5 hours at 0° C. the reaction mixture was partitioned between dichloromethane and water; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using Toluene yielded 18.1 g (90%) 11-bromoundecyl 3,5-dinitrobenzoate as yellow powder.

Workup

  1. customAfter 4.5 hours at 0° C. the reaction mixture was partitioned between dichloromethane and water
  2. washthe organic phase was washed repeatedly with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-1427393b133341b897ad4702d58ebef3
Source dataset
uspto-grants-2006_04
Patent number
US07034098B2

Reaction notes

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