2-Methoxyethylamine → HCID 70592352, compound

HRID 1732899Notes

Reaction equation

HRID 1732899 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].[N+:15]([CH:18]=[C:19](SC)SC)([O-:17])=[O:16].[CH3:24][O:25][CH2:26][CH2:27][NH2:28]>C(O)C>[CH3:24][O:25][CH2:26][CH2:27][NH:28][C:19]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[S:9][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:6][CH:7]=1)=[CH:18][N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 129139512-(5-Dimethylaminomethyl-2-thienylmethylthio)ethylamine

Product 1

HCID 70592352HCID 70592352, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[[[5-(N,N-Dimethylaminomethyl)2-thienyl]methyl]thio]ethanamine (4.3 g) and 1-nitro-2,2-bis(methylthio)ethylene (3.3 g) in ethanol (50 ml) were heated at reflux for 51/2 hr. Methoxyethylamine (1.8 ml) was added and the reaction heated at reflux for 22 hr. The solvent was removed and the residual oil was purified by column chromatography (silica/methanol). The resultant solid was recrystallised from isopropyl acetate to give the title compound as a white solid (1.04 g). m.p. 79°-80°. TLC silica/ethyl acetate, water, isopropanol, 0.88 ammonia 25:8:15:2, Rf 0.7.

Workup

  1. temperatureat reflux for 51/2 hr
  2. temperaturethe reaction heated
  3. temperatureat reflux for 22 hr
  4. customThe solvent was removed
  5. customthe residual oil was purified by column chromatography (silica/methanol)
  6. customThe resultant solid was recrystallised from isopropyl acetate

Sources & evidence

ORD record
ord-4e479986fb45405db7b203df5feb82a8
Source dataset
uspto-grants-1980_12
Patent number
US04239769

Reaction notes

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