Sodium hydride → 1-cyclopropylmethyl-7-methylsulfanyl-1H-benzoimidazole

HRID 657522ノート

反応式

HRID 657522 の反応式
[CH3:1][S:2][C:3]1[C:11]2[N:10]=[CH:9][NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:15][CH:16]1[CH2:18][CH2:17]1>CN(C=O)C>[CH:16]1([CH2:15][N:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([S:2][CH3:1])[C:11]=3[N:10]=[CH:9]2)[CH2:18][CH2:17]1.[CH:16]1([CH2:15][N:10]2[C:11]3[C:3]([S:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=3[N:8]=[CH:9]2)[CH2:18][CH2:17]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 251423217-(Methylthio)-1H-benzo[d]imidazole

生成物 2

HCID 594425971-cyclopropylmethyl-7-methylsulfanyl-1H-benzoimidazoleHCID 594426631-cyclopropylmethyl-4-methylsulfanyl-1H-benzoimidazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

2 g of 4-methylsulfanyl-1H-benzoimidazole were dissolved in 20 ml of dry DMF. 0.6 g of sodium hydride (60% strength in mineral oil) were added portionwise at 0° C. After stirring for 1 h at 20° C., the mixture was cooled to 0° C. and bromomethylcyclopropane (1.5 ml) was added. The reaction mixture was stirred for 18 h at 20° C. The solvent was evaporated in vacuo and the residue was taken up in water and EA (100 ml each). The phases were separated, the aqueous phase was extracted with EA, and the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography (100 g silica gel; DCM/EA, gradient from 100:0 to 80:20) to yield 1.2 g of 1-cyclopropylmethyl-4-methylsulfanyl-1H-benzoimidazole and 0.8 g of 1-cyclopropylmethyl-7-methylsulfanyl-1H-benzoimidazole.

後処理

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 18 h at 20° C
  3. customThe solvent was evaporated in vacuo
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with EA
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customThe crude product was purified by flash chromatography (100 g silica gel; DCM/EA, gradient from 100:0 to 80:20)

出典と根拠

ORDレコード
ord-b308309d1f014e869475e090f6ca6bf8
出典データセット
uspto-grants-2011_12
特許番号
US08076324B2

反応ノート

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