Thiazole → HCID 10774002, compound

HRID 1068917Notes

Reaction equation

HRID 1068917 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[S:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C([O-])(=O)C.[K+]>CC(N(C)C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:10]1[C:14]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:13][N:12]=[CH:11]1

Participants

6

Reactant 3

HCID 9256ThiazoleHCID 707414-BromobenzaldehydeHCID 517044Potassium Acetate

Product 1

HCID 10774002HCID 10774002, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

In a bomb tube, a mixture of 3.7 g (20 mmol) of 4-bromo-benzaldehyde, 6.64 ml (93 mmol) of thiazole, 2.94 g of potassium acetate and 1.16 g (1 mmol) of Pd(PPh3)4 is stirred in 50 ml of dimethylacetamide at 150° C. for 12 hours. The reaction mixture is concentrated by evaporation; water is added to the residue and the mixture is extracted three times with methylene chloride. The organic phases are filtered through cotton wadding, concentrated by evaporation and chromatographed (SiO2; hexane/ethyl acetate=1:2): 4-(Thiazol-5-yl)-benzaldehyde is obtained; HPLC:tRet(grad20-100/20)=11.4.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. additionwater is added to the residue
  3. extractionthe mixture is extracted three times with methylene chloride
  4. filtrationThe organic phases are filtered through cotton wadding
  5. concentrationconcentrated by evaporation
  6. customchromatographed (SiO2; hexane/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-2eaf8066ddab4dd99916e7261e1c6571
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

Loading…