2-Chloro-N,N-dimethylethylamine → HCID 20192358, compound

HRID 2118989Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[C:12]([CH2:17][CH3:18])=[N:13][O:14][C:15]=2[CH3:16])=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])[C:9]([C:11]2[C:12]([CH2:17][CH3:18])=[N:13][O:14][C:15]=2[CH3:16])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 22.0 grams (0.0887 mole) of N-m-fluorophenyl-3-ethyl-5-methyl-4-isoxazole carboxamide and 4.4 grams (0.0921 mole) of 50% sodium hydride in oil in 500 ml. of dimethylformamide is stirred at room temperature for five hours. The resulting mixture is treated by dropwise addition with 9.68 grams (0.09 mole) of 2-dimethylaminoethyl chloride). The resulting mixture is heated at 60° C. for 20 hours. The mixture is cooled, poured onto ice water and extracted with ether. The ether is washed with 2N hydrochloric acid and the aqueous acidic layer made basic with sodium hydroxide and extracted with methylene chloride. The methylene chloride extract is dried with magnesium sulfate and evaporated to give N-(m-fluorophenyl)-N-(2-dimethylaminoethyl)-3-ethyl-5-methyl-4-isoxazole carboxamide as an oil.

Workup

temperatureThe mixture is cooled
additionpoured onto ice water
extractionextracted with ether
washThe ether is washed with 2N hydrochloric acid
extractionextracted with methylene chloride
extractionThe methylene chloride extract
dry with materialis dried with magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-f7ac7c97e56d48b088c1bc3e30987411
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04681898

Reaction notes

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