Sodium hydride → HCID 18376462, compound

HRID 2300688Notes

Reaction equation

HRID 2300688 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][NH:6][C:7](=[O:28])[CH2:8][CH2:9][C:10]1[O:14][C:13]([N:15]2[CH:19]=[CH:18][N:17]=[C:16]2[CH3:20])=[N:12][C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1>CN(C)C=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:11]2[N:12]=[C:13]([N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[CH3:20])[O:14][C:10]=2[CH2:9][CH2:8][C:7]2[O:28][CH2:4][CH2:5][N:6]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18376445HCID 18376445, compound

Product 1

HCID 18376462HCID 18376462, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 265 mg) was gradually added to a solution of N-(2-chloroethyl)-4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionamide (1.30 g) in N,N-dimethylformamide (30 ml), at room temperature. After stirring at room temperature for 3 hours, the reaction mixture was poured into ice water, and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried (MgSO4), and the solvent was evaporated. The crystals thus precipitated were collected by filtration to obtain 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-[2-(2-oxazolin-2-yl)ethyl]oxazole (1.07 g, 91%). This was recrystallized from acetone-isopropyl ether to give colorless prisms. mp 119-120° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated
  5. customThe crystals thus precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8ac00fbbe7dc4ab6918b95a42d576859
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

Loading…