Methyl iodide → HCID 25219174, compound

HRID 1990871Notes

Reaction equation

HRID 1990871 reaction equation
[SH:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][C:5]=2[N:6]=1.[C:15]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:15][S:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:12])=[O:13])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178514691HCID 178514691, compound

Product 1

HCID 25219174HCID 25219174, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-mercapto-benzooxazole-5-sulfonic acid amide (17.0 g, 73.8 mmol, 1.0 equiv) in anhydrous DMF (200 mL) was added anhydrous K2CO3 (51.0 g, 369.1 mmol, 5.0 equiv) and methyl iodide (16.1 mL, 36.7 g, 258.4 mmol, 3.5 equiv). After stirring for 3 h at rt, the K2CO3 was removed by filtration and the reaction mixture concentrated by evaporation under reduced pressure. The residue was washed with ethyl acetate (50 mL) give 17.4 g (97%) of the title compound. 1H NMR (300 MHz, DMSO): δ 2.80 (s, 3H), 7.47 (br s, 2H), 7.83 (s, 2H), 8.07 (s, 1H). 13C NMR (75 MHz, DMSO): δ 4.28, 110.47, 115.71, 122.04, 140.99, 141.37, 152.92, 167.84. MS (ISP): 244.9 [M+H]+.

Workup

  1. customthe K2CO3 was removed by filtration
  2. concentrationthe reaction mixture concentrated by evaporation under reduced pressure
  3. washThe residue was washed with ethyl acetate (50 mL)

Sources & evidence

ORD record
ord-2f75b29e20f0418fba708c67c0299df1
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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