Benzothiazole → 2-(Tributylstannyl)-1,3-benzothiazole

HRID 2220121Notes

Reaction equation

HRID 2220121 reaction equation
C([Li])CCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>CCOCC>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:7]1[S:6][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 7222BenzothiazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 37623922-(Tributylstannyl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M, 10 mL, 15.98 mmol) was added to a solution of benzothiazole (1.80 g, 13.3 mmol) in anhydrous ether (30 ml) stirred at −78° C. under nitrogen. After 10 min, tri-n-butylstannyl chloride (4.33 g, 13.31 mmol) was added, then the solution was allowed to warm to room temperature, and stirred for another 1 h. The mixture was quenched and washed with 1N sodium hydroxide, dried through MgSO4, filtered, and evaporated to give the sub-title compound as a brown oily residue (5.0 g), which was used without further purification in the next step.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for another 1 h
  3. customThe mixture was quenched
  4. washwashed with 1N sodium hydroxide
  5. dry with materialdried through MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9890acb71d2f4827bd88e2b812d65f4c
Source dataset
uspto-grants-2008_08
Patent number
US07417050B2

Reaction notes

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