Triethylamine → 1-[2-[4-[(Methylsulfonyl)amino]phenyl]ethyl]-1H-imidazole

HRID 65256ノート

反応式

HRID 65256 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1)(=[O:25])=[O:24]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 35236744-[2-(1H-imidazol-1-yl)ethyl]aniline

生成物 1

HCID 137633971-[2-[4-[(Methylsulfonyl)amino]phenyl]ethyl]-1H-imidazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

To a -10° C. solution of 8 g (0.064 mole) of 1-[2-(4-aminophenyl)ethyl]-1H-imidazole and 10 mL triethylamine in 200 mL of methylene chloride add 5 mL of methanesulfonyl chloride dropwise. Stir the resulting solution at -10° C. for about 30 minutes then warm to ambient temperature for about 30 minutes. Wash the reaction mixture with water. (2×100 mL). Extract with 10% aqueous sodium hydroxide (2×50 mL). The combined aqueous extracts are neutralized with ammonium chloride then extracted with methylene chloride (2×100 mL) and combined. Remove the solvent in vacuo to provide the title compound, which may be recrystallized from tetrahydrofuran.

後処理

  1. temperaturethen warm to ambient temperature for about 30 minutes
  2. washWash the reaction mixture with water
  3. extractionExtract with 10% aqueous sodium hydroxide (2×50 mL)
  4. extractionthen extracted with methylene chloride (2×100 mL)
  5. customRemove the solvent in vacuo

出典と根拠

ORDレコード
ord-1675d0f43e1d4b2db8c66df17dee7637
出典データセット
uspto-grants-1986_09
特許番号
US04613609

反応ノート

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