1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-allyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 2427425Notes

Reaction equation

HRID 2427425 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH2:13]([C:16]1[C:23]([F:24])=[C:22]([F:25])[C:19]([CH2:20][OH:21])=[C:18]([F:26])[C:17]=1[F:27])[CH:14]=[CH2:15].[C:28]([C:30]([CH3:40])=[CH:31][C@@H:32]1[C@@H:34]([C:35](O)=[O:36])[C:33]1([CH3:39])[CH3:38])#[N:29]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:28]([C:30]([CH3:40])=[CH:31][C@@H:32]1[C@@H:34]([C:35]([O:21][CH2:20][C:19]2[C:18]([F:26])=[C:17]([F:27])[C:16]([CH2:13][CH:14]=[CH2:15])=[C:23]([F:24])[C:22]=2[F:25])=[O:36])[C:33]1([CH3:39])[CH3:38])#[N:29]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12944013[2,3,5,6-Tetrafluoro-4-(prop-2-en-1-yl)phenyl]methanolHCID 66664531(1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 866520804-allyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere, 0.23 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to a mixture of 0.20 g of 4-allyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.16 g of (1R)-trans-3-(2-cyano-1-propeny)-2,2-dimethylcyclopropanecarboxylic acid, 0.05 g of 4-dimethylaminopyridine and 4 ml of anhydrous chloroform, and the mixture was stirred at room temperature for 3 hours. Thereafter, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate two times. Ethyl acetate layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.32 g of 4-allyl-2,3,5,6-tetrafluorobenzyl(1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate represented by the following formula:

Workup

  1. extractionfollowed by extraction with ethyl acetate two times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b57dcb34b9a3497cad4b1bcac7cc5cf5
Source dataset
uspto-grants-2011_06
Patent number
US07968598B2

Reaction notes

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