Methyl iodide → HCID 66861357, compound

HRID 252993Notes

Reaction equation

HRID 252993 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH3:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C:19]2[S:23][C:22]([SH:24])=[N:21][N:20]=2)=[C:13]([N+:25]([O-:27])=[O:26])[CH:12]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([C:19]2[S:23][C:22]([S:24][CH3:1])=[N:21][N:20]=2)=[C:13]([N+:25]([O-:27])=[O:26])[CH:12]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178488245HCID 178488245, compound

Product 1

HCID 66861357HCID 66861357, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (13.8 mg, 1.0 mmol) and 0.0624 ml (1.0 mmol) of methyl iodide were added to a solution of 150 mg (0.510 mmol) of 5-(4,5-dimethoxy-2-nitrophenyl)-1,3,4-thiadiazole-2-thiol produced in Reference Example 2 in N,N-dimethylformamide (2 ml), and the mixture was stirred at room temperature for 10 min. The mixture was diluted with 30 ml of ethyl acetate, and the diluted solution was washed with 30 ml of a 10% aqueous ammonium chloride solution and 30 ml of saturated brine. The organic layer was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure, and the resultant crystal was washed with diisopropyl ether to give 140 mg (yield 89%) of the title compound.

Workup

  1. washthe diluted solution was washed with 30 ml of a 10% aqueous ammonium chloride solution and 30 ml of saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationwas then filtered
  4. concentrationThe filtrate was concentrated under the reduced pressure
  5. washthe resultant crystal was washed with diisopropyl ether

Sources & evidence

ORD record
ord-b83f512b870840dbb453ebbb4cef2a44
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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