2,2-Diethoxyethylamine → N-(2,2-Diethoxyethyl)-1-(methylsulfanyl)-2-nitroethen-1-amine

HRID 1979729Notes

Reaction equation

HRID 1979729 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].[N+:10]([CH:13]=[C:14](SC)[S:15][CH3:16])([O-:12])=[O:11]>C(O)C>[N+:10]([CH:13]=[C:14]([S:15][CH3:16])[NH:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 71398340N-(2,2-Diethoxyethyl)-1-(methylsulfanyl)-2-nitroethen-1-amineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a)(i) A solution of aminoacetaldehyde diethylacetal (8 g, 0.06 mol) and 1-nitro-2,2-bis-methylthioethylene (10 g, 0.06 mol) in ethanol (100 ml) was refluxed for 20 hours. The solvent was removed in vacuo. The residue was chromatographed on a silica gel column eluted with carbon tetrachloride/chloroform (7:3) and the product was crystallised from propan-2-ol to give 1-nitro-2-methylthio-2-(2,2-diethoxyethylamino)ethylene (8.7 g, 58%) m.p. 73°-73.5°.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was chromatographed on a silica gel column
  3. washeluted with carbon tetrachloride/chloroform (7:3)
  4. customthe product was crystallised from propan-2-ol

Sources & evidence

ORD record
ord-c87fdbabe0b04aa38e0f8b89a1e16f8d
Source dataset
uspto-grants-1984_11
Patent number
US04482563

Reaction notes

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