Dimethylformamide → 2-(Methylthio)-6-nitro-1,3-benzothiazole

HRID 1791936Notes

Reaction equation

HRID 1791936 reaction equation
[H-].[Na+].[SH:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:7]=2[N:8]=1.[CH3:16]N(C=O)C>>[CH3:16][S:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 178418579HCID 178418579, compound

Product 1

HCID 3055522-(Methylthio)-6-nitro-1,3-benzothiazole

Procedure

Sodium hydride (containing by 60%, 6.15 g) was suspended in DMF (120 mL) and 2-mercapto-6-nitrobenzothiazole (20 g) was added thereto under ice-cooling. After completion of bubbling, methyl iodide (26.4 mL) was added thereto. The mixture was stirred at room temperature for 18 hr. Water (800 mL) was added to the reaction mixture, and the precipitated solid was collected by filtration to give 2-methylthio-6-nitrobenzothiazole (21.2 g) as a pale-yellow powder.

Workup

  1. temperatureunder ice-cooling
  2. customAfter completion of bubbling
  3. additionmethyl iodide (26.4 mL) was added
  4. additionWater (800 mL) was added to the reaction mixture
  5. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-4de3f2addb3c4a68bcd3fc84a411955c
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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