1,1-Bis(methylthio)-2-nitroethylene → 1-Nitro-2-(2-propynylamino)-2-{2-[(4-bromo-1H-imidazol-5-yl)methylthio]ethylamino}ethylene

HRID 27388Notes

Reaction equation

HRID 27388 reaction equation
Br[C:2]1[N:3]=CN[C:6]=1[CH2:7]SCCN.CSC(SC)=C[N+]([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].C(N)C#C>>[N+:21]([CH:24]=[C:25]([NH:3][CH2:2][C:6]#[CH:7])[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 239041PropargylamineHCID 127889492-(((5-Bromo-1H-imidazol-4-yl)methyl)thio)ethanamineHCID 705440301-nitro-2-methylthio-2-{2-[(4-bromo-1H-imidazol-5-yl)methylthio]ethylamino}ethylene

Product 1

HCID 740425911-Nitro-2-(2-propynylamino)-2-{2-[(4-bromo-1H-imidazol-5-yl)methylthio]ethylamino}ethylene

Procedure

When 2-[(4-bromo-1H-imidazol-5-yl)methylthio]ethylamine (prepared according to the procedure described in Belgian Patent 779,775) is reacted with 1,1-bis(methylthio)-2-nitroethylene according to the procedure of Example 6, Step A, and the resultant 1-nitro-2-methylthio-2-{2-[(4-bromo-1H-imidazol-5-yl)methylthio]ethylamino}ethylene is treated with propargylamine by the procedure of Example 6, Step B, the title compound is produced.

Sources & evidence

ORD record
ord-e1f318a89eca4f00abc225cae3408126
Source dataset
uspto-grants-1980_09
Patent number
US04221737

Reaction notes

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