Sodium hydride → 4-Tert-butyl-2-[5-(3-cyanophenylmethoxy)benzofuran-2-yl]thiazole

HRID 487681Notes

Reaction equation

HRID 487681 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28]>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:23][C:24]4[CH:31]=[CH:30][CH:29]=[C:26]([C:27]#[N:28])[CH:25]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 108586652-(4-Tert-butylthiazol-2-yl)-5-hydroxybenzofuran

Product 1

HCID 190927074-Tert-butyl-2-[5-(3-cyanophenylmethoxy)benzofuran-2-yl]thiazoleYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of 4-tert-butyl 2-(5-hydroxybenzofuran-2-yl)thiazole (0.33 g) in N,N-dimethylformamide (5 ml), sodium hydride ((60% in mineral oil) 55 mg) was added below 10° C. After being stirred for 10 minutes, 3-bromomethylbenzonitrile (0.26 g) was added to the mixture. After being stirred at ambient temperature for 2 hours, the resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was crystallized with diisopropyl ether and filtered to give crystals of 4-tert-butyl-2-[5-(3-cyanophenylmethoxy)benzofuran-2-yl]thiazole (0.38 g).

Workup

  1. stirringAfter being stirred at ambient temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. customThe syrup was crystallized with diisopropyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-c322be4785b847fdb6a9c5661f3b8496
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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