3,5-Dimethylpyrazole → 2-Chloro-5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-1,3-thiazole

HRID 38678

Reaction equation

HRID 38678 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[H-].[Na+].[Cl:10][C:11]1[S:12][C:13]([CH2:16]Cl)=[CH:14][N:15]=1>CN(C=O)C>[Cl:10][C:11]1[S:12][C:13]([CH2:16][N:3]2[C:2]([CH3:1])=[CH:6][C:5]([CH3:7])=[N:4]2)=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 62103,5-DimethylpyrazoleHCID 24758Sodium hydrideHCID 27631792-Chloro-5-chloromethylthiazole

Product 1

HCID 37350872-Chloro-5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

A solution of 3,5-dimethyl-1H-pyrazole (Aldrich, 114 mg, 1.190 mmol) in DMF (5 ml) was added over NaH (Aldrich, 34.3 mg, 1.42 mmol) at 0° C. under N2 atmosphere. The mixture was stirred during 5 min and 2-chloro-5-(chloromethyl)-1,3-thiazole (AK scientific, 200 mg, 1.19 mmol) in DMF (2 ml) was added. The mixture was allowed to stir overnight. Finally, it was heated to 50° C. for 1 h. DMF was eliminated by washing with 14 ml of a mixture EtOAc/NH4Cl 1N (1:1). The organic layer was dried over Na2SO4 and the solution concentrated to dryness under vacuum, to afford a crude product which was chromatographed (silica gel cartridge, Hex/EtOAc) yielding the title compound. 1H NMR (300 MHz, CDCl3) δ ppm: 7.37 (s, 1H); 5.82 (s, 1H), 5.26 (s, 2H); 2.24 (s, 3H); 2.22 (s, 3H). [ES+MS] m/z: 228.1 (MH+).

Workup

  1. stirringto stir overnight
  2. washby washing with 14 ml of a mixture EtOAc/NH4Cl 1N (1:1)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationthe solution concentrated to dryness under vacuum
  5. customto afford a crude product which
  6. customwas chromatographed (silica gel cartridge, Hex/EtOAc)

Sources & evidence

ORD record
ord-f253babd52bc4cb6996371bb3ab806b7
Source dataset
uspto-grants-2013_09
Patent number
US08524750B2

Linked notes

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