Dimethylamine → HCID 86736909, compound

HRID 2049145Notes

Reaction equation

[CH3:1][CH:2]([C:15]1([O:20][CH2:19]1)[C:16](O)=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:21]([N:23](CC)[CH2:24]C)C.ClC(OCC)=O.N(CC)(CC)CC.Cl.CNC>O1CCCC1>[CH3:21][N:23]([CH3:24])[C:16](=[O:17])[C:15]1([CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:1])[O:20][CH2:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.42 g (0.005 mole) of 2-tetradecylglycidic acid in 10 ml of tetrahydrofuran (THF) at 0° C. (ice-water bath) with stirring is added 0.50 g (0.005 mole) of triethylamine in a small amount of THF. The solution is stirred at 0° C. for 30 minutes and 0.51 g (0.005 mole) of ethyl chloroformate is added. The mixture is stirred at about 0° C. (ice-water bath) for 3 hours (ppt. of Et3N.HCl observed). At the end of 3 hours 0.429 g (0.015 mole) of dimethyl amine in THF is added and the mixture stirred overnight (16 hours) at room temperature. The THF solvent is concentrated to about 1/3 its volume, water is added and the mixture extracted with ether. The ether extract is dried over Na2SO4 and the ether solvent removed. A crude oily residue is obtained which is purified by column chromatography on silica gel. A 37.8% yield of pure N,N-dimethyl-2-tetradecylglycidamide is obtained, m.p. 40°-42° C.

Workup

stirringthe mixture stirred overnight (16 hours) at room temperature
concentrationThe THF solvent is concentrated to about 1/3 its volume, water
additionis added
extractionthe mixture extracted with ether
extractionThe ether extract
dry with materialis dried over Na2SO4
customthe ether solvent removed
customA crude oily residue is obtained which
customis purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-485709f041824e14a0f9efd20ebf6ca5
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04196300

Reaction notes

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