Dimethylformamide → N,N-Dimethyl-N′-octylmethanimidamide

HRID 615433Notes

Reaction equation

HRID 615433 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.S(OC)(OC)(=O)=O.[CH2:13]([NH2:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][N:2]([CH3:5])[CH:3]=[N:21][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 8143OctylamineHCID 14798Sodium Hydroxide

Product 1

HCID 12498110N,N-Dimethyl-N′-octylmethanimidamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Dimethylformamide (8.8 g, 0.12 mole), dimethyl sulfate (19.3 g, 0.15 mole) and toluene (20 ml) were placed in a 100 ml round bottom flask and heated at reflux for 30 minutes. During this time a light brown oil separated. The reaction was cooled to room temperature and the toluene was decanted. The dimethylformamide/dimethyl sulfate complex was washed with dry toluene (2×20 ml) and the toluene was decanted. n-Octylamine (15.5 g, 0.12 mole) in toluene (20 ml) was added rapidly with stirring. The reaction temperature rose briefly to 60° C. The reaction was stirred for 90 minutes, then extracted with a solution of sodium hydroxide (7.2 g, 0.18 mole) in water (40 ml). The organic phase was washed with brine (40 ml), dried over anhydrous Na2SO4, and filtered. GLC showed the product to be about 72% pure after concentration.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. customDuring this time a light brown oil separated
  4. customthe toluene was decanted
  5. washThe dimethylformamide/dimethyl sulfate complex was washed with dry toluene (2×20 ml)
  6. customthe toluene was decanted
  7. customrose briefly to 60° C
  8. stirringThe reaction was stirred for 90 minutes
  9. washThe organic phase was washed with brine (40 ml)
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationpure after concentration

Sources & evidence

ORD record
ord-5030bdd099894d2d9c554d5d798f4405
Source dataset
uspto-grants-1985_02
Patent number
US04499274

Reaction notes

Loading…