4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → 1-nitro-2-methylthio-2-{2-[(4-methyl-1H-imidazol-5-yl)methylthio]ethylamino}ethylene

HRID 436854Notes

Reaction equation

HRID 436854 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[CH3:12][S:13]([C:15](SC)=[CH:16][N+:17]([O-:19])=[O:18])=O>CO>[N+:17]([CH:16]=[C:15]([S:13][CH3:12])[NH:11][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1])([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 704568641-nitro-2-methylthio-2-{2-[(4-methyl-1H-imidazol-5-yl)methylthio]ethylamino}ethyleneYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-[(5-methyl-4-imidazolyl)methylthio]ethylamine (8.56 g) in methanol (115 ml) was added dropwise over 13 minutes to a stirred solution of 1-methylsulphinyl-1-methylthio-2-nitroethylene (9.06 g) in methanol (150 ml) at 40°. Evaporation of the reaction mixture and recrystallisation of the resultant solid from isopropanol yielded the title product (7.15 g), m.p. 147°-150°.

Workup

  1. customEvaporation of the reaction mixture and recrystallisation of the resultant solid from isopropanol

Sources & evidence

ORD record
ord-6e544182d166492eb0e2cdd604bf0311
Source dataset
uspto-grants-1977_06
Patent number
US04028379

Reaction notes

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