Tetraethyltin → 7-Ethyl-5-nitro-1,3-benzothiazole

HRID 1489132

Reaction equation

HRID 1489132 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.[CH2:14]([Sn](CC)(CC)CC)[CH3:15]>CCOC(C)=O>[CH2:14]([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)[CH3:15]

Participants

4

Reactant 2

HCID 11704TetraethyltinHCID 227280317-Bromo-5-nitrobenzothiazole

Product 1

HCID 227280367-Ethyl-5-nitro-1,3-benzothiazoleYield 75.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-bromo-5-nitrobenzothiazole (0.15 g, 0.58 mmol), tetraethyltin (0.18 mL, 0.87 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 91 mg (0.44 mmol, 75%) 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-98013f6c225846cc946819d9a2d8a790
Source dataset
uspto-grants-1997_10
Patent number
US05677321

Linked notes

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