1-Methylthio-1-methylamino-2-nitroethylene → N-[2-[[[2-(hydroxymethyl)-4-thiazolyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

HRID 1736661Notes

Reaction equation

HRID 1736661 reaction equation
[CH3:1][NH:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[NH2:10][CH2:11][CH2:12][S:13][CH2:14][C:15]1[N:16]=[C:17]([CH2:20][OH:21])[S:18][CH:19]=1>CN(C=O)C>[OH:21][CH2:20][C:17]1[S:18][CH:19]=[C:15]([CH2:14][S:13][CH2:12][CH2:11][NH:10][C:3]([NH:2][CH3:1])=[CH:4][N+:5]([O-:7])=[O:6])[N:16]=1

Participants

4

Reactant 2

HCID 1235491-Methylthio-1-methylamino-2-nitroethyleneHCID 196122374-[[(2-Aminoethyl)thio]-methyl]-2-hydroxymethylthiazole

Product 1

HCID 67557601N-[2-[[[2-(hydroxymethyl)-4-thiazolyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.11 g of 2-methylamino-2-methylthio-1-nitroethylene was added to a solution of 15.81 g of 4-[[(2-aminoethyl)thio]-methyl]-2-hydroxymethylthiazole in 190 ml of DMF. The solution was stirred at room temperature for 4 days. The reaction mixture was concentrated under reduced pressure to give a residue which was chromatographed on silica gel eluting with 5-10% methanol in acetonitrile to give 12.8 g (61%) of N-[2-[[[2-(hydroxymethyl)-4-thiazolyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue which
  3. customwas chromatographed on silica gel eluting with 5-10% methanol in acetonitrile

Sources & evidence

ORD record
ord-eaa4208da2af4d41bb1f2ebba7786e65
Source dataset
uspto-grants-1996_07
Patent number
US05541335

Reaction notes

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