Sodium hydride → HCID 18376486, compound

HRID 2300692Notes

Reaction equation

HRID 2300692 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][NH:6][C:7](=[O:29])[CH2:8][CH2:9][CH2:10][C:11]1[O:15][C:14]([N:16]2[CH:20]=[CH:19][N:18]=[C:17]2[CH3:21])=[N:13][C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1>CN(C)C=O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:12]2[N:13]=[C:14]([N:16]3[CH:20]=[CH:19][N:18]=[C:17]3[CH3:21])[O:15][C:11]=2[CH2:10][CH2:9][CH2:8][C:7]2[O:29][CH2:4][CH2:5][N:6]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18376488HCID 18376488, compound

Product 1

HCID 18376486HCID 18376486, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oil, 130 mg) was gradually added to a N,N-dimethylformamide solution (30 ml) of N-(2-chloroethyl)-4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutyramide (870 mg) at room temperature. After stirring for 4 hours at room temperature, the reaction mixture was poured into ice water. And this was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-[3-(2-oxazolin-2-yl)propyl]oxazole (615 mg, 78%) was obtained by evaporating the solvent. This was recrystallized from acetone-isopropyl ether to give colorless prisms. mp 88-89° C.

Workup

  1. extractionAnd this was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-bfe06c7dbf654822afdef96d3ffca73c
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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