Methyl iodide → HCID 65197767, compound

HRID 1497425Notes

Reaction equation

HRID 1497425 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)=[N:2]1.IC.[C:15](=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCCC>CN(C=O)C>[CH3:15][N:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)=[N:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 178519821HCID 178519821, compound

Product 1

HCID 65197767HCID 65197767, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1H-pyrazol-3-yl)thiazole-5-carbaldehyde (0.25 g, 1.3 mmol) was dissolved in DMF (5 mL) and iodomethane (0.26 mL, 4.1 mmol) and potassium carbonate (0.6 g, 4.1 mmol) were added. The reaction was stirred for 3 h at room temperature until the reaction was deemed complete by TLC (80% EtOAc\hexane). The reaction was poured into ice water (50 mL), and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated under vacuum to afford 2-(1-methyl-1H-pyrazol-3-yl)thiazole-5-carbaldehyde as a yellow solid (0.1 g, 38% yield). 1H-NMR (DMSO-d6): δ 10.0 (s, 1H) 8.60 (s, 1H). 8.50 (s, 1H), 8.05 (s, 1H), 3.89 (s, 3H); LC-MS m/z calcd for [M+H]+, 194.03. found, 194.1.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8e8b0c09df4a439e80f96e370d74cdca
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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