1,1-Bis(methylthio)-2-nitroethylene → 1-Nitro-2-[2-(2-pyridylmethylthio)ethylamino]-2-[2-((4-bromo-5-imidazolyl)methylthio)ethylamino]ethylene

HRID 1679405Notes

Reaction equation

HRID 1679405 reaction equation
BrC1N=CNC=1CSCCN.[N+](C=C(SC)SC)([O-])=O.[N+:21]([CH:24]=[C:25](SC)[NH:26][CH2:27][CH2:28][S:29][CH2:30][C:31]1[NH:35][CH:34]=[N:33][C:32]=1[Br:36])([O-:23])=[O:22].[NH2:39][CH2:40][CH2:41][S:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1>>[N+:21]([CH:24]=[C:25]([NH:39][CH2:40][CH2:41][S:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)[NH:26][CH2:27][CH2:28][S:29][CH2:30][C:31]1[NH:35][CH:34]=[N:33][C:32]=1[Br:36])([O-:23])=[O:22]

Participants

5

Reactant 4

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 127889492-(((5-Bromo-1H-imidazol-4-yl)methyl)thio)ethanamineHCID 128894012-((2-Aminoethyl)thiomethyl)pyridineHCID 705440301-nitro-2-methylthio-2-{2-[(4-bromo-1H-imidazol-5-yl)methylthio]ethylamino}ethylene

Product 1

HCID 706245091-Nitro-2-[2-(2-pyridylmethylthio)ethylamino]-2-[2-((4-bromo-5-imidazolyl)methylthio)ethylamino]ethylene

Procedure

When 4-bromo-5-[(2-aminoethyl)thiomethyl]imidazole (from the dihydrobromide (4.8 g)) is reacted with 1nitro-2,2-bis-methylthioethylene (2.0 g) according to the procedure of Example 8(i) and the resultant 1-nitro-2-methylthio-2-[2-((4-bromo-5-imidazolyl)methylthio)ethylamino]ethylene reacted with 2-[(2-aminoethyl)thiomethyl]pyridine by the procedure of Example 1(a)(ii), the title compound is produced.

Sources & evidence

ORD record
ord-e8950678aa6c45e0be126c69ed7774d2
Source dataset
uspto-grants-1978_03
Patent number
US04080459

Reaction notes

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