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

HRID 1829145Notes

Reaction equation

HRID 1829145 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-86a0d844ddcf4903a5d8340b2fceed02
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

Loading…