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

HRID 2086061Notes

Reaction equation

HRID 2086061 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 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 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-1906920c36ce428b90560989136ac913
Source dataset
uspto-grants-2004_04
Patent number
US06723741B2

Reaction notes

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