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

HRID 1275102Notes

Reaction equation

HRID 1275102 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-14279251615c4d0cac0d1ce3b6cab923
Source dataset
uspto-grants-2000_12
Patent number
US06159998

Reaction notes

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