6-Nitrobenzothiazole → 7-Methyl-6-nitro-1,3-benzothiazole

HRID 617262Notes

Reaction equation

HRID 617262 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:13][Mg+].[Br-]>C(Cl)(Cl)Cl>[CH3:13][C:5]1[C:6]2[S:10][CH:9]=[N:8][C:7]=2[CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 762566-NitrobenzothiazoleHCID 178418689HCID 178418689, compound

Product 1

HCID 125888347-Methyl-6-nitro-1,3-benzothiazoleYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6-nitrobenzothiazole (1.4 g, 7.7 mmol) in 50 mL of TMF was added 5.1 mL of MeMgBr (15.3 mmol) dropwise in 0.5 h period at 0° C. The reaction mixture was then stirred for additional 2 h. It was quenched by adding THF solution of 2,3-dichloro-5,6-dicyanobenzoquinone until the color of the solution turns to dark green. The reaction mixture was concentrated in vacuo to yield a dark solid which was subjected to column chromatography (CHCl3, neat) to provide 0.68 g (3.5 mmol, 46%) of the desired product.

Workup

  1. customIt was quenched
  2. additionby adding THF solution of 2,3-dichloro-5,6-dicyanobenzoquinone until the color of the solution
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto yield a dark solid which

Sources & evidence

ORD record
ord-1b1b64e10f3546afb1ac2e3f6676dc75
Source dataset
uspto-grants-1999_09
Patent number
US05948804

Reaction notes

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