Dimethylformamide → n-Propyl-5-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2-carboxylate

HRID 2248883Notes

Reaction equation

HRID 2248883 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[CH2:21]([O:24][C:25]([C:27]1[O:28][C:29]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][C:30]=2[N:31]=1)=[O:26])[CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(C)=O>[CH2:21]([O:24][C:25]([C:27]1[O:28][C:29]2[CH:35]=[CH:34][C:33]([O:36][CH2:2][C:3]3[CH:20]=[CH:19][CH:18]=[C:5]([O:6][CH2:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)[CH:4]=3)=[CH:32][C:30]=2[N:31]=1)=[O:26])[CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 86745010n-Propyl-5-hydroxybenzoxazole-2-carboxylate

Product 1

HCID 54376787n-Propyl-5-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.47 g of 2-((3-chloromethylphenoxy)methyl)quinoline, 2.7 g of n-propyl-5-hydroxybenzoxazole-2carboxylate, 1.69 g of potassium carbonate and 1 ml of dimethylformamide is refluxed in 50 ml of acetone for 41 hours. The mixture is concentrated in vacuo and the residue is dissolved in water. This solution is neutralized with diluted hydrochloric acid and the resulting solid is filtered off and purified by flash silica gel chromatography in propanol-dimethylformamide to give n-propyl-5-(3-(quinolin-2-ylmethyloxy)benzyloxy)-benzoxazole-2-carboxylate

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in water
  3. filtrationthe resulting solid is filtered off
  4. custompurified by flash silica gel chromatography in propanol-dimethylformamide

Sources & evidence

ORD record
ord-bb7c9cf92bb643b8b174d07ec706f313
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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