Dimethylamine → N,N-Dimethyl-N′-octylmethanimidamide

HRID 615434Notes

Reaction equation

HRID 615434 reaction equation
S(OC)(OC)(=O)=O.[CH3:8][N:9]([CH3:12])[CH:10]=O.[CH2:13]([NH2:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].CNC.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:8][N:9]([CH3:12])[CH:10]=[N:21][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 8143OctylamineHCID 14798Sodium Hydroxide

Product 1

HCID 12498110N,N-Dimethyl-N′-octylmethanimidamideYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Dimethyl sulfate (34.7 g, 0.27 mole) was placed in a 300 ml 3-necked round bottom flask equipped with a heating mantle, magnetic stirrer, thermometer, addition funnel and calcium chloride drying tube. The reaction was stirred and warmed to 50° C. Heating was discontinued and dimethyl formamide (26 g, 0.36 mole) was added over a 10 minute period. The reaction temperature gradually rose to 85° C. The reaction was stirred an additional hour during which time the temperature fell to 45° C. The reaction was cooled and maintained between 0° and 10° C. while n-octylamine (32.3 g, 0.25 mole) in toluene (50 ml) was added over a period of 15 minutes. After the addition was complete, the addition funnel and drying tube were replaced by a dry ice/acetone condenser and gas inlet tube. The cooling bath was removed and gaseous dimethylamine (6.1 g, 0.14 mole) was added over a period of about 5 minutes. The reaction was stirred at room temperature for 1 hour. The reaction was extracted with sodium hydroxide (12.5 g, 0.31 mole) in water (50 ml), washed with brine (25 ml), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 44.5 g (97 %) of the title compound as a very light yellow liquid. GLC showed 99.6% of volatiles in a single peak.

Workup

  1. customequipped with a heating mantle, magnetic stirrer
  2. additionthermometer, addition funnel and calcium chloride drying tube
  3. temperatureHeating
  4. customgradually rose to 85° C
  5. stirringThe reaction was stirred an additional hour during which time the temperature
  6. customfell to 45° C
  7. temperatureThe reaction was cooled
  8. additionwas added over a period of 15 minutes
  9. additionAfter the addition
  10. customthe addition funnel and drying tube
  11. customwere replaced by a dry ice/acetone condenser and gas inlet tube
  12. customThe cooling bath was removed
  13. stirringThe reaction was stirred at room temperature for 1 hour
  14. washwashed with brine (25 ml)
  15. dry with materialdried over anhydrous sodium sulfate
  16. filtrationfiltered
  17. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca3162e405d246ed8844e320390b36f3
Source dataset
uspto-grants-1985_02
Patent number
US04499274

Reaction notes

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