Benzothiazole → 2-(Tributylstannyl)-1,3-benzothiazole
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.[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]>O1CCCC1>[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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of benzothiazole (30.7 g) in tetrahydrofuran (700 ml), which was cooled at −78° C., was added dropwise n-butyllithium (2.5M solution in hexane) (100 ml) under a nitrogen atmosphere, the solution was stirred for 10 minutes at −78° C. Tributyltin chloride (77.9 g) was added dropwise thereto, the solution was stirred for 1.5 hours at −78° C., and then stirred for 2 hours while warming from −78° C. to room temperature. The reaction mixture was concentrated in vacuo, diethyl ether (400 ml) was added thereto, insoluble material was removed by filtration, and then the solvent was evaporated in vacuo. The residue was purified by distillation in vacuo (0.5 mmHg, 170 to 184° C.) to provide the title compound (73.0 g).
Workup
- stirringthe solution was stirred for 1.5 hours at −78° C.
- stirringstirred for 2 hours
- temperaturewhile warming from −78° C. to room temperature
- concentrationThe reaction mixture was concentrated in vacuo, diethyl ether (400 ml)
- additionwas added
- custominsoluble material was removed by filtration
- customthe solvent was evaporated in vacuo
- distillationThe residue was purified by distillation in vacuo (0.5 mmHg, 170 to 184° C.)
Sources & evidence
- ORD record
- ord-36d057748b644c338625faa9471fb216
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399520B2
Reaction notes
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