Dimethyl Sulfoxide → 4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole
Reaction equation
[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]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- waitat 80° for an additional hour
- temperaturethe resulting mixture was heated at 70°-80° for 4 hours
- customthe triphenyl phosphine was removed by filtration
- extractionThe filtrate was extracted with 100 ml
- dry with materialdried (MgSO4)
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-cb1ee3e0d85f49028f59fb31004d75d9
- Source dataset
- uspto-grants-1978_10
- Patent number
- US04119781
Reaction notes
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