Methyl iodide → HCID 19391754, compound

HRID 1926411Notes

Reaction equation

HRID 1926411 reaction equation
[F:1][C:2]1[C:10]2[S:9][C:8]([SH:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:12]I>[OH-].[Na+]>[F:1][C:2]1[C:10]2[S:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178505565HCID 178505565, compound

Product 1

HCID 19391754HCID 19391754, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a well-stirred solution of 7-fluoro-2-mercaptobenzothiazole (1.0 g, 5.4 mmol) in 10% aq. NaOH (10 mL) was added methyl iodide (2.14 g, 2.8 eq) dropwise, and the reaction mixture was stirred at rt for 30 min. A yellowish solid was collected by filtration, washed with cold water, and dissolved in ethyl acetate (50 mL). The EtOAc solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound. 1H-NMR (CDCl3, 300 MHz): δ=7.66 (d, J=8.1 Hz, 1H), 7.40-7.33 (m, 1H), 7.04-6.97 (m, 1H), 2.80 (s, 3H).

Workup

  1. filtrationA yellowish solid was collected by filtration
  2. washwashed with cold water
  3. dissolutiondissolved in ethyl acetate (50 mL)
  4. dry with materialThe EtOAc solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2844cd7b87de49c9ae841635b2c8fc4f
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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