Ethylene Oxide → HCID 20322512, compound

HRID 840005Notes

Reaction equation

HRID 840005 reaction equation
[CH2:1]([C:3]1([CH3:27])[NH:22][C:21]([CH2:24][CH3:25])([CH3:23])[CH2:20][C:5]2([NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6]2=[O:19])[CH:4]1[CH3:26])[CH3:2].[CH2:28]1[O:30][CH2:29]1>CO.Cl>[CH2:1]([C:3]1([CH3:27])[N:22]([CH2:28][CH2:29][OH:30])[C:21]([CH2:24][CH3:25])([CH3:23])[CH2:20][C:5]2([NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6]2=[O:19])[CH:4]1[CH3:26])[CH3:2]

Participants

5

Reactant 2

HCID 6354Ethylene OxideHCID 20322535HCID 20322535, compound2×

Product 1

HCID 20322512HCID 20322512, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6.0 g of 7,9-diethyl-6,7,9-trimethyl-3-octyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (Compound 5) obtained as described in Example 4, in 40 ml of methanol were added 3 drops of concentrated hydrochloric acid and 3.5 g of ethylene oxide. The mixture was heated at 110° C for 24 hours in a sealed tube and then concentrated to give 6.5 g of Compound 118 as an oil. This product had an Rf value of 0.33 on thin layer chromatography on a 0.25 mm thick layer of silica gel (Kieselgel 60F 254, available from Merck & Co.; eluent, benzene containing 5% of triethylamine).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-a3d84470103c40a1820caca10150dcb0
Source dataset
uspto-grants-1978_06
Patent number
US04097587

Reaction notes

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