Phosphorus oxychloride → HCID 18376433, compound

HRID 2300663Notes

Reaction equation

HRID 2300663 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH:27]=[CH:26][N:25]=[C:24]3[CH3:28])[O:16][C:17]=2[CH2:18][CH2:19][C:20]([NH2:22])=O)=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH:27]=[CH:26][N:25]=[C:24]3[CH3:28])[O:16][C:17]=2[CH2:18][CH2:19][C:20]#[N:22])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 53894997HCID 53894997, compound

Product 1

HCID 18376433HCID 18376433, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride(585 mg) was added dropwise into a N,N-dimethylformamide solution (20 ml) of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionamide(840 mg) at room temperature. After stirring for 1 hour, the reaction mixture was poured into ice water, and neutralized with saturated sodium bicarbonate. The precipitating crystals are collected by filtration to give 4-(4-chlorophenyl)-5-(2-cyanoethyl)-2-(2-methyl-1-imidazolyl)oxazole(650 mg, 82%). This was recrystallized with acetone-isopropyl ether to give colorless prisms. mp 163-164° C.

Workup

  1. filtrationThe precipitating crystals are collected by filtration

Sources & evidence

ORD record
ord-aceeaf42ef1d476ba1dd8e5a7c4c5bfe
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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