Diethyl Ether → HCID 14424276, compound

HRID 414222Notes

Reaction equation

HRID 414222 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[S:6][C:7]([CH3:10])=[CH:8][CH:9]=1)=[O:4].[CH2:11]1[N:16]2[CH2:17][N:18]3[CH2:20][N:14]([CH2:15]2)[CH2:13][N:12]1[CH2:19]3.C(OCC)C>C(Cl)(Cl)Cl.C(Cl)Cl>[Br-:1].[O:4]=[C:3]([C:5]1[S:6][C:7]([CH3:10])=[CH:8][CH:9]=1)[CH2:2][N+:12]12[CH2:13][N:14]3[CH2:20][N:18]([CH2:17][N:16]([CH2:15]3)[CH2:11]1)[CH2:19]2

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 4101HexamethylenetetramineHCID 122897372-Bromo-1-(5-methyl-2-thienyl)ethanone

Product 1

HCID 14424276HCID 14424276, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-1-(5-methylthien-2-yl)ethanone (30.0 g of the aforesaid dark liquid) and hexamethylene tetramine (21.0 g, 0.15 mole) in chloroform (500 ml) was stirred at room temperature for three days. The solvent was removed from the reaction mixture by evaporation under reduced pressure, leaving a dark residue. This residue was stirred in warm methylene chloride. Diethyl ether was added slowly to the mixture, causing a solid to precipitate. After being cooled for several hours, the solid was collected by filtration. The filter cake was rinsed with diethyl ether and was dried under reduced pressure yielding 43.1 g of 1-[2-oxo-2-(5-methylthienyl)ethyl]-3,5,7-triaza-1-azoniatricyclo-[3,3,1,13,7 ]decane bromide (mp 141° C. dec).

Workup

  1. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure
  2. customleaving a dark residue
  3. customto precipitate
  4. temperatureAfter being cooled for several hours
  5. filtrationthe solid was collected by filtration
  6. washThe filter cake was rinsed with diethyl ether
  7. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-51558efb2e724ccc8c8f6c59ae0ef28c
Source dataset
uspto-grants-1988_12
Patent number
US04791124

Reaction notes

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