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

HRID 27389Notes

Reaction equation

HRID 27389 reaction equation
OC[C:3]1[N:4]=CN[C:7]=1[CH2:8]SCCN.CSC(SC)=C[N+]([O-])=O.[N+:22]([CH:25]=[C:26](SC)[NH:27][CH2:28][CH2:29][S:30][CH2:31][C:32]1[NH:36][CH:35]=[N:34][C:33]=1[CH2:37][OH:38])([O-:24])=[O:23].C(N)C#C>>[N+:22]([CH:25]=[C:26]([NH:4][CH2:3][C:7]#[CH:8])[NH:27][CH2:28][CH2:29][S:30][CH2:31][C:32]1[NH:36][CH:35]=[N:34][C:33]=1[CH2:37][OH:38])([O-:24])=[O:23]

Participants

5

Reactant 4

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 239041PropargylamineHCID 129515302-[(5-Hydroxymethyl-1H-imidazol-4-yl)methylthio]ethylamineHCID 705894051-nitro-2-methylthio-2-{2-[(4-hydroxymethyl-1H-imidazol-5-yl)methylthio]ethylamino}ethylene

Product 1

HCID 740425961-Nitro-2-(2-propynylamino)-2-{2-[(4-hydroxymethyl-1H-imidazol-5-yl)methylthio]ethylamino}ethylene

Procedure

When 2-[(4-hydroxymethyl-1H-imidazol-5-yl)methylthio]-ethylamine [prepared according to the procedure described in Belgian Pat. No. 843,840] 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-hydroxymethyl-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-561d46c7b5e4437a9b421a6accee19cf
Source dataset
uspto-grants-1980_09
Patent number
US04221737

Reaction notes

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