Tetramethyltin → 7-Methyl-5-nitro-1,3-benzothiazole

HRID 2300406Notes

Reaction equation

HRID 2300406 reaction equation
Br[C:2]1[C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][Sn](C)(C)C>CCOC(C)=O>[CH3:14][C:2]1[C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 11661TetramethyltinHCID 227280317-Bromo-5-nitrobenzothiazole

Product 1

HCID 227280277-Methyl-5-nitro-1,3-benzothiazoleYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-bromo-5-nitrobenzothiazole (0.15 g, 0.58 mmol), tetramethyltin (0.20 mL, 0.1.5 mmol) and catalytic amount of Cl2Pd(PPh3)2 in a sealed tube was stirred for 12 h at 90° C. The reaction mixture was diluted with EtOAc and washed with brine several times. Organic solution was dried over Na2SO4 and concentrated in vacuo, yielding an oil which was subjected to column chromatography (EtOAc, neat) to provide 65 mg (0.32 mmol, 67%) of the desired product.

Workup

  1. washwashed with brine several times
  2. dry with materialOrganic solution was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customyielding an oil which

Sources & evidence

ORD record
ord-23f7e9c342a14786bb6ef5e7395f3489
Source dataset
uspto-grants-2002_12
Patent number
US06498177B2

Reaction notes

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