Potassium Iodide → n-Propyl 5-chloro-4-(4-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2-carboxylate

HRID 2248887Notes

Reaction equation

HRID 2248887 reaction equation
Cl[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][C:28]([C:30]([O:32][CH2:33][CH2:34][CH3:35])=[O:31])=[N:27][C:26]=2[C:36]=1[OH:37].[I-].[K+]>CC(C)=O.CN(C)C=O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][C:28]([C:30]([O:32][CH2:33][CH2:34][CH3:35])=[O:31])=[N:27][C:26]=2[C:36]=1[O:37][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 147741632-(4-Chloromethylphenoxy)methylquinolineHCID 19994790HCID 19994790, compound

Product 1

HCID 53653363n-Propyl 5-chloro-4-(4-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

0.78 g of 2-(4-chloromethylphenoxy)methylquinoline, 6.84 g of n-propyl 5-chloro-4-hydroxybenzoxazole-2carboxylate and a catalytic amount of potassium iodide are combined in 50 ml of acetone and 2 ml of dimethylformamide, and refluxed for 19 hours. The crude solid obtained on cooling is purified by flash chromatography to give n-propyl 5-chloro-4-(4-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2-carboxylate.

Workup

  1. customThe crude solid obtained
  2. temperatureon cooling
  3. customis purified by flash chromatography

Sources & evidence

ORD record
ord-d3ac78475dbe49ff9993f407b9c8f4c7
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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