Dimethylformamide → N-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]phthalimide

HRID 584375Notes

Reaction equation

HRID 584375 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][CH2:7][C:8]1[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:11][C:12]=1[CH3:13].[OH:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:13][C:12]1[O:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:9][C:8]=1[CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH:22]=[CH:21][CH:20]=1)[CH2:2][O:23][N:24]1[C:25](=[O:34])[C:26]2=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]2[C:28]1=[O:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

Product 1

HCID 11732904N-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]phthalimideYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(3-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (8.00 g), N-hydroxyphthalimide (4.13 g), potassium carbonate (7.05 g) and N,N-dimethylformamide (80 ml) was stirred at room temperature for 20 hours and water (800 ml) was added. The resultant crystals were filtered and washed with water to obtain N-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]phthalimide (10.1 g, yield 90%) as pale-brown crystals. m.p. 146-147° C.

Workup

  1. filtrationThe resultant crystals were filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-89e7219463454e1f9ab343014eb0490c
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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