1,1-Bis(methylthio)-2-nitroethylene → 1-Nitro-2-methylthio-2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]ethylene

HRID 1679396Notes

Reaction equation

HRID 1679396 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([Br:12])=[CH:10][CH:9]=[CH:8][N:7]=1.[N+:13]([CH:16]=[C:17](SC)[S:18][CH3:19])([O-:15])=[O:14]>C(#N)C>[N+:13]([CH:16]=[C:17]([S:18][CH3:19])[NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[C:11]([Br:12])=[CH:10][CH:9]=[CH:8][N:7]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 129515272-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amine

Product 1

HCID 706239951-Nitro-2-methylthio-2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]ethylene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(b)(i) A solution of 2-[(2-aminoethyl)thiomethyl]-3-bromopyridine (from the dihydrobromide, 3.0 g) and 1-nitro-2,2-bis-methylthioethylene (1.21 g) in acetonitrile (30 ml) was set aside at room temperature for 3 days. The product was chromatographed on a column of silica gel with elution by ethyl acetate, to give 1-nitro-2-methylthio-2-[2-((3-bromo-2-pyridyl)methylthio)ethylamino]ethylene (1.2 g), m.p. 79°-80° (from ethanol-ether).

Workup

  1. customThe product was chromatographed on a column of silica gel with elution by ethyl acetate

Sources & evidence

ORD record
ord-f4a9df18644149eab246e283d4bd3801
Source dataset
uspto-grants-1978_03
Patent number
US04080459

Reaction notes

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