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

HRID 1489130Notes

Reaction equation

HRID 1489130 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 Cl2 Pd(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-23e20ca550614b88a1eeb6ecaf6711ed
Source dataset
uspto-grants-1997_10
Patent number
US05677321

Reaction notes

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