Triethylamine → HCID 14836227, compound

HRID 1087763Notes

Reaction equation

HRID 1087763 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9].[CH2:10]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH3:11].C(N(CC)CC)C>C1COCC1.O>[CH2:10]([O:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:2][CH2:3][N:4]([CH2:8][CH2:7][OH:6])[C:5]1=[O:9])[CH3:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22720Propanolamine ethyl etherHCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-one

Product 1

HCID 14836227HCID 14836227, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.5 g of 3-(2-chloroethyl)oxazolidin-2-one, 4.57 g of 3-ethoxypropylamine and 10 g of triethylamine was refluxed for 10 hours, diluted with THF and water. The organic layer was worked up to give 5.13 g of 1-(3-ethoxypropyl)-3-(2-hydroxyethyl)imidazolidin-2-one, b.p. 110° C./0.5 mm. This material was methylated with 4.26 g of iodomethane and 1.13 g of NaH (60% in oil) in 60 ml of THF as mentioned under Example 22. This gave 3.9 g (71.4%) of oil, b.p. 100°-105° C./0.5 mm.

Workup

  1. temperaturewas refluxed for 10 hours

Sources & evidence

ORD record
ord-ce34e7d7f900406f8108904cd1450963
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

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