Methyl iodide → Ethyl 7-formyl-6-methyl-2-(methylthio)pyrazolo[5,1-b]thiazole-3-carboxylate

HRID 41255Notes

Reaction equation

HRID 41255 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][N:6]1[C:10](Cl)=[C:9]([CH:12]=[O:13])[C:8]([CH3:14])=[N:7]1)[CH3:2].[OH-].[K+].[C:18](=[S:20])=[S:19].[CH3:21]I>CS(C)=O>[CH:12]([C:9]1[C:8]([CH3:14])=[N:7][N:6]2[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])=[C:18]([S:20][CH3:21])[S:19][C:10]=12)=[O:13]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 737985ethyl 2-(5-chloro-4-formyl-3-methyl-1H-pyrazol-1-yl)acetate

Product 1

HCID 3507588Ethyl 7-formyl-6-methyl-2-(methylthio)pyrazolo[5,1-b]thiazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of ethyl(5-chloro-4-formyl-3-methyl-1H-pyrazol-1-yl)acetate (560 mg, 2.43 mmol), potassium hydroxide (495 mg, 7.5 mmol) and DMSO (9.72 mL) was added carbon disulfide (194 μL, 3.21 mmol), and the mixture was stirred at room temperature for 18 hours. To the reaction mixture, methyl iodide (182 μL, 2.92 mmol) was added, and the mixture was further stirred at room temperature for 8 hours. This reaction mixture was poured into ice water to yield a solid, and the obtained solid was filtered, and then washed with water and dried to obtain the title compound (346.1 mg, 1.22

Workup

  1. stirringthe mixture was further stirred at room temperature for 8 hours
  2. customto yield a solid
  3. filtrationthe obtained solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4fc206117a124bfe8a8d7c0a53feda75
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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