Acetic Acid → (5-Bromo-3-indolylmethyl)-trimethylammonium Methyl Sulfate

HRID 330278

反応式

HRID 330278 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][N:12]([CH3:14])[CH3:13].[C:15](O)(=O)C.[S:19]([O:24]C)([O:22][CH3:23])(=[O:21])=[O:20]>C1COCC1>[CH3:23][O:22][S:19]([O-:24])(=[O:21])=[O:20].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][N+:12]([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 176Acetic Acid2 回HCID 6497Dimethyl SulfateHCID 13249Indole, 5-bromo-3-(dimethylamino)methyl-

生成物 1

HCID 19869668(5-Bromo-3-indolylmethyl)-trimethylammonium Methyl Sulfate収率 391.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

According to the procedure of C. Huebner et al., J. Am. Chem. Soc., 75, 5887 (1953), a solution of 5-bromo-3-(dimethylaminomethyl)indole (28.3 g, 0.11 mol) and acetic acid (1.60 mL, 0.028 mol) in dry THF (154 mL) was added dropwise over a 1/2 hour period to a solution of dimethyl sulfate (52.04 mL, 0.55 mol) and acetic acid (1.60 mL, 0.028 mol) in dry THF (62 mL), keeping the temperature between 10°-15° C. The reaction was cooled in an ice bath for 1 hour, filtered, washed thoroughly with ether, and air dried for 1 hour to yield 41.6 g (100%) of product as a white solid. This was used immediately in the next step.

後処理

  1. custombetween 10°-15° C
  2. temperatureThe reaction was cooled in an ice bath for 1 hour
  3. filtrationfiltered
  4. washwashed thoroughly with ether, and air
  5. customdried for 1 hour

出典と根拠

ORDレコード
ord-f03b5aa07974412ab4ff8e0605ab640a
出典データセット
uspto-grants-1990_01
特許番号
US04895860

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