Dimethylamine → HCID 5271199, compound

HRID 544616Notes

Reaction equation

HRID 544616 reaction equation
Cl[C:2]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[CH:17]=2)=[CH:6][CH:5]=1)=[O:3].[CH3:24][NH:25][CH3:26]>C1(C)C=CC=CC=1>[CH3:24][N:25]([CH3:26])[C:2](=[O:3])[C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[CH:17]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 20458446HCID 20458446, compound

Product 1

HCID 5271199HCID 5271199, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 8.0 g of 5-[7-(4-chlorocarbonylphenoxy)heptyl]-3-methylisoxazole in 50 ml of dry toluene was saturated with dimethylamine gas over a 30 minute period. The reaction mixture was concentrated in vacuo, and the residue was dissolved in ether. The ether solution was boiled, treated with petroleum ether until turbid and cooled to produce 6.0 g of N,N-dimethyl-4-[7-(3-methyl-5-isoxazolyl)heptyloxy]benzamide, m.p. 58°-59° C.; MIC vs. polio-2 virus in vitro=2.5 μg/ml.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ether
  3. additiontreated with petroleum ether until turbid
  4. temperaturecooled

Sources & evidence

ORD record
ord-53151e1bba3a456793e0698dc3337f68
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

Loading…