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

HRID 1112020

반응식

HRID 1112020 반응식
[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]

참가 물질

10

반응물 7

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb1ee3e0d85f49028f59fb31004d75d9
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04119781

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