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

HRID 1433846
ノート
印刷プレビュー

反応式

HRID 1433846 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7222BenzothiazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

生成物 1

HCID 37623922-(Tributylstannyl)-1,3-benzothiazole収率 75.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  1. stirringthe solution was stirred for 1.5 hours at −78° C.
  2. stirringstirred for 2 hours
  3. temperaturewhile warming from −78° C. to room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo, diethyl ether (400 ml)
  5. additionwas added
  6. custominsoluble material was removed by filtration
  7. customthe solvent was evaporated in vacuo
  8. distillationThe residue was purified by distillation in vacuo (0.5 mmHg, 170 to 184° C.)

出典と根拠

ORDレコード
ord-6cb384d47d4b4554a4e2cddfbf8cda0d
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612114B2

反応ノート

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