Dimethylformamide → HCID 69025225, compound

HRID 1865767Notes

Reaction equation

HRID 1865767 reaction equation
[C:1](Cl)(=[O:23])[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][CH2:20][CH2:21][CH3:22].[N:25]1([CH2:30][CH:31]([OH:33])[CH3:32])[CH:29]=[CH:28][N:27]=[CH:26]1.CN(C)C=O>C1(C)C=CC=CC=1>[C:1]([O:33][CH:31]([CH3:32])[CH2:30][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1)(=[O:23])[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][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 109233alpha-Methyl-1H-imidazole-1-ethanolHCID 4104741Docosanoyl chloride

Product 1

HCID 69025225HCID 69025225, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

With ice cooling and stirring, 35.9 g of behenic chloride (16) was added to a mixture of 12.6 g of 1-(1H-imidazol-1-yl)-2-propanol (15) and 50 g of dimethylformamide. Then the mixture was stirred at room temperature for 2 hours. Toluene was added to the solution, followed by neutralization. Subsequent standard aqueous work-up and purification by column chromatography gave 41.3 g of [2-(1H-imidazol-1-yl)-1-methylethyl] behenate (Quencher 1). Yield 92%.

Workup

  1. stirringThen the mixture was stirred at room temperature for 2 hours
  2. customSubsequent standard aqueous work-up and purification by column chromatography

Sources & evidence

ORD record
ord-70e9103f9b7b4191add427c0c06b9783
Source dataset
uspto-grants-2009_12
Patent number
US07629108B2

Reaction notes

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