4-Hydroxybenzaldehyde → 2-(4-Formylphenoxy)-5-thiazolecarboxamide

HRID 747556Notes

Reaction equation

HRID 747556 reaction equation
Cl[C:2]1[S:3][C:4]([C:7]([NH2:9])=[O:8])=[CH:5][N:6]=1.[OH:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:15]([C:14]1[CH:17]=[CH:18][C:11]([O:10][C:2]2[S:3][C:4]([C:7]([NH2:9])=[O:8])=[CH:5][N:6]=2)=[CH:12][CH:13]=1)=[O:16]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 534244962-Chloro-1,3-thiazole-5-carboxamide

Product 1

HCID 586773822-(4-Formylphenoxy)-5-thiazolecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 2-chlorothiazole-5-carboxamide (0.771 g, 4.78 mmol) and 4-hydroxybenzaldehyde (0.584 g, 4.78 mmol) in DMF (15.9 mL). Add K2CO3 (1.651 g, 11.95 mmol) and heat at 100° C. for 2 hours. Concentrate the reaction mixture. Take the solid up in dichloromethane:methanol (5:1). Add ethyl acetate to precipitate out a white solid. Filter and collect the solid as the title compound: 1H NMR (DMSO): 10.00 (s, 1H), 8.11 (s, 1H), 8.02 (d, J=8.4 Hz, 2H), 7.94 (s, 1H), 7.59 (d, J=8.8 Hz, 2H), 7.41 (s, 1H); HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=11.4 min, 98.2% purity.

Workup

  1. concentrationConcentrate the reaction mixture
  2. customAdd ethyl acetate to precipitate out a white solid
  3. filtrationFilter
  4. customcollect the solid as the title compound
  5. customHPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=11.4 min, 98.2% purity

Sources & evidence

ORD record
ord-9ad4a1f5a0134548b6bc301522964335
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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