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

HRID 1732606Notes

Reaction equation

HRID 1732606 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]([CH3:17])=O)([O-:12])=[O:11]>CO>[N+:10]([CH:13]=[C:14]([S:15][CH3:17])[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 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 71398340N-(2,2-Diethoxyethyl)-1-(methylsulfanyl)-2-nitroethen-1-amineYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of aminoacetaldehyde diethylacetal (11g, 0.08 mol) and 1-nitro-2-methylthio-2-methylsulphinyl-ethylene (15g, 0.08 mol) in methanol (200 ml) was stirred for 21/2 hours at room temperature. The solvent was removed in vacuo leaving a yellow oily residue which after trituration with propan-2-ol gave 1-nitro-2-methylthio-2-(2,2-diethoxy-ethylamino)ethylene (9.8, 49%) m.p. 72-74°.

Workup

  1. customThe solvent was removed in vacuo
  2. customleaving a yellow oily residue which after trituration with propan-2-ol

Sources & evidence

ORD record
ord-54d4c138c89046aa90702c41bbb48096
Source dataset
uspto-grants-1980_12
Patent number
US04238494

Reaction notes

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