N,N-dimethyl-2-Furanmethanamine → HCID 20199141, compound

HRID 652109

Reaction equation

HRID 652109 reaction equation
[CH3:1][N:2]([C:11](SC)=[N:12][C:13](=O)[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:3]=CC1C=CC=CC=1.[CH3:22][N:23]([CH3:30])[CH2:24][C:25]1[O:26][CH:27]=[CH:28][CH:29]=1>C(#N)C>[CH3:22][N:23]([CH2:24][C:25]1[O:26][C:27]([CH2:18][S:15][CH2:14][CH2:13][NH:12][C:11]2[N:2]([CH3:1])[N:3]=[C:13]([CH2:14][S:15]([CH3:18])(=[O:16])=[O:17])[N:12]=2)=[CH:28][CH:29]=1)[CH3:30]

Participants

4

Reactant 2

HCID 84478N,N-dimethyl-2-FuranmethanamineHCID 70434558HCID 70434558, compound

Product 1

HCID 20199141HCID 20199141, compoundYield 135.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Methyl 1-methyl-N-[(methylsulphonyl)acetyl]-2-(phenylmethylene)hydrazinecarboximidothioate (1.05 g) and 5-[[2-aminoethyl)thio]methyl]-N,N-dimethylfuranmethanamine (0.85 g)in acetonitrile (3 ml) were heated on a steam bath at atmospheric pressure for 5 minutes then under water vacuum for 10 minutes. The oily residue was dissolved in acetonitrile (3 ml) and the solution re-evaporated under water vacuum. The oily residue was dissolved in 2N hydrochloric acid (3 ml) and 5N hydrochloric acid (4 ml) added to the solution. The solution was heated on a steam bath for 15 minutes and after cooling to room temperature, water (10 ml) was added and the oily suspension extracted with ethyl acetate. The aqueous phase was basified with sodium carbonate and the oily suspension extracted with ethyl acetate to yield an oil (0.84 g). This was chromatographed (using solvent system D) to give the title compound (0.78 g) as an oil. T.l.c. System D, Rf 0.5.

Workup

  1. customthe solution re-evaporated under water vacuum
  2. dissolutionThe oily residue was dissolved in 2N hydrochloric acid (3 ml)
  3. addition5N hydrochloric acid (4 ml) added to the solution
  4. temperatureThe solution was heated on a steam bath for 15 minutes
  5. additionwater (10 ml) was added
  6. extractionthe oily suspension extracted with ethyl acetate
  7. extractionthe oily suspension extracted with ethyl acetate

Sources & evidence

ORD record
ord-5aa710dd1dd7493a801e0d6426adbcce
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Linked notes

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