5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 67860895, compound

HRID 1073319Notes

Reaction equation

HRID 1073319 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].[O:15]([C:22](OC1C=CC=CC=1)(OC1C=CC=CC=1)[CH2:23][N+:24]([O-:26])=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:22]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:23][N+:24]([O-:26])=[O:25])=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 12509339HCID 12509339, compound

Product 1

HCID 67860895HCID 67860895, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

21·4 g (0·1 mol) of 2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamine and 35·1 g (0·1 mol) of 1,1,1-triphenoxy-2-nitroethane are boiled for 3 hours in 250 ml of acetonitrile under a nitrogen atmosphere. The solvent is evaporated off under vacuum after cooling to 40° C. and the yellow oil left behind is chromatographed on 560 g of silica gel with dichloromethane/methanol (95:5). After concentration by evaporation under vacuum, the main fraction yields 28·7 g (76%) of the title compound in the form of a yellowish, viscous oil.

Workup

  1. customThe solvent is evaporated off under vacuum
  2. waitthe yellow oil left behind
  3. customis chromatographed on 560 g of silica gel with dichloromethane/methanol (95:5)
  4. concentrationAfter concentration
  5. customby evaporation under vacuum

Sources & evidence

ORD record
ord-e58e15b2540c4b24ae082d7e4904ab4e
Source dataset
uspto-grants-1990_11
Patent number
US04968808

Reaction notes

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