Dimethyl Sulfoxide → 4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

HRID 1112020

反応式

HRID 1112020 の反応式
[C:1](S(O)=O)([NH2:3])=[NH:2].[H-].[Na+].[Na].N[CH2:11][CH2:12]S.[CH3:14][O-].[Na+].Cl.Cl.[NH2:19][CH2:20]CS.[CH3:23][S:24]([CH3:26])=O>O.CO>[NH2:19][CH2:20][CH2:23][S:24][CH2:26][C:14]1[N:2]=[CH:1][NH:3][C:11]=1[CH3:12]

参加物

10

反応物 7

HCID 679Dimethyl SulfoxideHCID 6058CysteamineHCID 24758Sodium hydrideHCID 61274Thiourea dioxideHCID 5360545SodiumHCID 101541332-aminoethanethiol DihydrochlorideHCID 10942334Sodium Methoxide

生成物 1

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Triphenyl β-acetylvinylphosphonium bromide (4.11 g., 0.01 mole) was added in one portion to a stirred suspension of 1.1 g. (0.01 mole) of formamidine sulfinic acid in 20 ml. of dimethylsulfoxide containing 0.25 g. of sodium hydride. The mixture was stirred at ambient temperature for 1 hour then at 80° for an additional hour. A solution of 0.99 g. (0.01 mole) of the sodium salt of cysteamine, prepared by addition of two equivalents of sodium methoxide to cysteamine dihydrochloride, in 10 ml. of methanol was added and the resulting mixture was heated at 70°-80° for 4 hours. The mixture was diluted with twice its volume of water and the triphenyl phosphine was removed by filtration. The filtrate was extracted with 100 ml. of toluene and with two 100 ml. portions of chloroform. The chloroform extracts were combined, dried (MgSO4) and evaporated to dryness to give 4-(2-aminoethyl)thiomethyl-5-methylimidazole.

後処理

  1. waitat 80° for an additional hour
  2. temperaturethe resulting mixture was heated at 70°-80° for 4 hours
  3. customthe triphenyl phosphine was removed by filtration
  4. extractionThe filtrate was extracted with 100 ml
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-cb1ee3e0d85f49028f59fb31004d75d9
出典データセット
uspto-grants-1978_10
特許番号
US04119781

関連ノート

読み込み中…