Methyl iodide → 2-(Methylthio)-5-nitrobenzo[d]oxazole

HRID 1174916Notes

Reaction equation

HRID 1174916 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[S:12])[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:17]>C1COCC1>[CH3:17][S:12][C:10]1[O:11][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7862935-Nitrobenzo[D]Oxazole-2-Thiol

Product 1

HCID 152521182-(Methylthio)-5-nitrobenzo[d]oxazoleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Suspend 5-nitro-3H-benzooxazole-2-thione (5.15 g, 26.3 mmol) in THF (150 mL). Cool in an ice bath to 5° C. and add sodium hydride (60% dispersion in mineral oil) (1.7 g, 42.5 mmol). Stir for 15 min at 5° C. Add dropwise iodomethane (5.0 mL, 80.1 mmol) dissolved in THF (30 mL) over 1 h. Continue to stir at room temperature for 4 h. Absorb the reaction mixture onto silica gel, and purify using silica gel chromatography, eluting with a gradient of EtOAc in hexane (0-60%) to afford the title compound (4.75 g, 86%). 1H NMR (400 MHz, DMSOd6): δ 8.47 (d, 1H, J=3.1 Hz), 8.24 (dd, 1H, J=9.0, 2.4 Hz), 7.89 (d, 1H, J=8.8 Hz), 2.81 (s, 3H).

Workup

  1. stirringto stir at room temperature for 4 h
  2. customAbsorb the reaction mixture onto silica gel
  3. custompurify
  4. washeluting with a gradient of EtOAc in hexane (0-60%)

Sources & evidence

ORD record
ord-379434f402a54fd9a549c83385c39f75
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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