Chloroform → HCID 12096929, compound

HRID 1841621Notes

Reaction equation

HRID 1841621 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].Cl.[OH:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[CH:26](Cl)(Cl)Cl>CN(C)CCN.O1CCCC1>[CH:20]1([CH2:19][CH2:18][N:17]([CH2:16][CH2:15][OH:14])[C:1]([NH:8][CH2:12][CH2:11][N:10]([CH3:9])[CH3:26])=[O:2])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 682631,1'-CarbonyldiimidazoleHCID 22723091HCID 22723091, compound

Product 1

HCID 12096929HCID 12096929, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 66053N,N-DimethylethylenediamineSolvent

Procedure

1,1′-Carbonyldiimidazole (0.43 g) was dissolved in a solution of 2-(dimethylamino) ethylamine (0.19 g) in anhydrous tetrahydrofuran (11 ml) in the nitrogen gas atmosphere and the resulting solution was stirred at room temperature for 20 minutes. To the reaction solution, there was added N-(2-hydroxyethyl)-2-cyclohexyl ethylamine hydrochloride (0.50 g) and the mixture was refluxed with heating for 3 hours. Chloroform was added to the reaction solution with ice cooling, followed by washing the mixture with saturated sodium hydrogen carbonate aqueous solution and then with saturated sodium chloride aqueous solution, drying over anhydrous magnesium sulfate and concentrating under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to thus give the title compound (Compound 1-1, 0.68 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 3 hours
  3. washby washing the mixture with saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialwith saturated sodium chloride aqueous solution, drying over anhydrous magnesium sulfate
  5. concentrationconcentrating under reduced pressure
  6. customThe resulting oily product was purified through the silica gel column chromatography

Sources & evidence

ORD record
ord-f4bd15b6020d49cd9d1b603a73eceb94
Source dataset
uspto-grants-2004_01
Patent number
US06683200B2

Reaction notes

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