4-Hydroxybenzaldehyde → 4-(1,3-thiazol-4-ylmethoxy)benzaldehyde

HRID 1721678Notes

Reaction equation

HRID 1721678 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[S:17]1[CH:21]=[C:20]([CH2:22]Cl)[N:19]=[CH:18]1>CN(C=O)C.[Cl-].[Na+].O>[S:17]1[CH:21]=[C:20]([CH2:22][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[N:19]=[CH:18]1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochloride

Product 1

HCID 8209774-(1,3-thiazol-4-ylmethoxy)benzaldehydeYield 80.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (12.1 g, 100 mmol) and potassium carbonate (41.5 g, 0.30 mole) in DMF (100 mL) was added 4-thiazolylmethyl chloride hydrochloride (17.0 g, 100 mmol), and the resulting mixture was stirred at ambient temperature for 48 hours. The mixture was then poured into brine and filtered to collect the precipitated solid. The solid was washed with water (500 mL) and 10% ethyl ether in hexane and dried in vacuo to provide 17.6 g of 4-(4-thiazolylmethoxy)benzaldehyde.

Workup

  1. filtrationfiltered
  2. customto collect the precipitated solid
  3. washThe solid was washed with water (500 mL) and 10% ethyl ether in hexane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5d8f4fbefcd648af8f56452a86f999d4
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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