Potassium Carbonate → HCID 14645091, compound

HRID 1032666Notes

Reaction equation

HRID 1032666 reaction equation
Cl.[CH3:2][N:3]([CH2:15][CH2:16]Cl)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:2][N:3]([CH2:15][CH2:16][S:27][C:24]1[CH:25]=[CH:26][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=1)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 158094-NitrobenzenethiolHCID 19915718HCID 19915718, compound

Product 1

HCID 14645091HCID 14645091, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[N-Methyl-N-(4-nitrophenethyl)amino]ethyl chloride hydrochloride (3.0 g), 4-nitrothiophenol (1.7 g) and potassium carbonate (4.0 g) in acetonitrile (100 ml) were stirred at reflux for 16 hours. After evaporation, the residue was partitioned between water and ethyl acetate. The organic liquors were washed with saturated aqueous brine, dried (MgSO4), filtered and evaporated to give an orange oil (3.6 g). Chromatography on silica ("Kieselgel 60"-Trade Mark) eluting with ethyl acetate followed by collection of suitable fractions gave on evaporation the title compound as a yellow solid, (3.05 g), m.p. 56°-7°.

Workup

  1. temperatureat reflux for 16 hours
  2. customAfter evaporation
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe organic liquors were washed with saturated aqueous brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9ce48b91d4fb4d4eb46872cca944926c
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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