2-(2-Aminoethylthiomethyl)-3-ethoxypyridine → 1-Methylthio-1-[2-(3-ethoxy-2-pyridylmethylthio)ethylamino]-2-nitroethylene

HRID 262464Notes

Reaction equation

HRID 262464 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][N:7]=1.[CH3:15][S:16][C:17](S(C)=O)=[CH:18][N+:19]([O-:21])=[O:20]>CO>[CH3:15][S:16][C:17]([NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][N:7]=1)=[CH:18][N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 204022362-(2-Aminoethylthiomethyl)-3-ethoxypyridineHCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 705100751-Methylthio-1-[2-(3-ethoxy-2-pyridylmethylthio)ethylamino]-2-nitroethyleneYield 49.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-(2-Aminoethylthiomethyl)-3-ethoxypyridine (2.2 g) in methanol (35 cc) was added over 25 minutes to a stirred solution of 1-methylthio-1-methylsulphinyl-2-nitroethylene (2.07 g) in methanol (85 ml) at 27°-30°, and the mixture was left overnight at room temperature. The mixture was evaporated to a residual oil which was triturated with ethanol/ether to give 1-methylthio-1-[2-(3-ethoxy-2-pyridylmethylthio)ethylamino]-2-nitroethylene (1.68 g) m.p. 126°-127°.

Workup

  1. customThe mixture was evaporated to a residual oil which
  2. customwas triturated with ethanol/ether

Sources & evidence

ORD record
ord-730997f662ae4ab291bee26ebbb9e608
Source dataset
uspto-grants-1979_05
Patent number
US04154838

Reaction notes

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