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

HRID 2223999Notes

Reaction equation

HRID 2223999 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li]CCCC.[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]>C1COCC1>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=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 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

20 ml of freshly distilled THF was flushed for 30 min with a stream of nitrogen after which benzothiazole (1.0 g, 7.4 mmol) was added. After being flushed for another 30 min, the solution was cooled to −78° C. and placed under inert nitrogen atmosphere. 0.9 equivalents of n-BuLi (2 M solution in hexane, 2.66 ml, 6.66 mmol) was added dropwise over a period of 30 min, during which the solution turned to deep red. The solution was kept at −78° C. for 1 h and then tri-n-butyltin chloride (2.0 mi, 7.4 mmol) was added dropwise over a period of 1 h. During this addition, the solution shifted from deep red to brownish yellow, then to greenish blue and finally to light brown. After yet another hour at −78° C., the solution was allowed to reach room temperature. The THF was removed on a rotary evaporator and the product, a yellow oil, was isolated by distillation in vacuo. Yield: 2.47 g, 79%. 1H NMR (CDCl3): δ 0.90 (t, J═S, 9H, Bu3Sn), 1.29 (in, 6H, Bu3Sn), 1.35 (m, 6H, Bu3Sn), 1.63 (t, J=8, 6H, Bu3Sn), 7.37 (t, J=8, 1H, ArH), 7.46 (t, J=8, 1H, ArH, 7.96 (d, J=8, 1H, ArH), 8.17 (D, J=8, 1H, ArH).

Workup

  1. additionwas added
  2. customAfter being flushed for another 30 min
  3. additionDuring this addition
  4. waitAfter yet another hour at −78° C.
  5. customto reach room temperature
  6. customThe THF was removed on a rotary evaporator
  7. customthe product, a yellow oil, was isolated by distillation in vacuo

Sources & evidence

ORD record
ord-4b1b05e9dda64ff894b5be0ee20d290b
Source dataset
uspto-grants-2008_05
Patent number
US07378240B2

Reaction notes

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