Chloroform → HCID 86634951, compound

HRID 1665207Notes

Reaction equation

HRID 1665207 reaction equation
[OH:1][CH2:2][N:3]1[C:7](=[O:8])[CH2:6][N:5]([CH2:9][C:10]#[CH:11])[C:4]1=[O:12].[CH2:13]([O:15][N:16]=[CH:17]/[C:18](/[CH3:28])=[CH:19]/[C@@H:20]1[C@@H:22]([C:23](O)=[O:24])[C:21]1([CH3:27])[CH3:26])[CH3:14].C(Cl)(Cl)Cl.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.[Cl-].[Na+].O>[CH2:13]([O:15][N:16]=[CH:17]/[C:18](/[CH3:28])=[CH:19]/[C@@H:20]1[C@@H:22]([C:23]([O:1][CH2:2][N:3]2[C:7](=[O:8])[CH2:6][N:5]([CH2:9][C:10]#[CH:11])[C:4]2=[O:12])=[O:24])[C:21]1([CH3:27])[CH3:26])[CH3:14]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117895972,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)-HCID 86634952HCID 86634952, compound

Product 1

HCID 86634951HCID 86634951, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

Under nitrogen atmosphere, to a mixture of 0.44 g of 3-hydroxymethyl-1-(2-propynyl)imidazolidine-2,4-dione, 0.58 g of (1R)-trans-3-[(E)-3-ethoxyimino-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid, catalytic amount of 4-dimethylaminopyridine and 5 ml of anhydrous chloroform was added 0.50 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the mixture was stirred at room temperature overnight. Thereafter, saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then, filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.34 g of 2,5-dioxo-3-(2-propynyl)imidazolidin-1-ylmethyl (1R)-trans-3-[(E)-3-ethoxyimino-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylate (hereinafter, referred to as the present compound (2)) represented by the formula (2):

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb1c9ae24bbe485f8ecf931a9429ab12
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

Loading…