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

HRID 615432Notes

Reaction equation

HRID 615432 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].[OH-].[Na+]>O.C1(C)C=CC=CC=1>[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

7

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 8143OctylamineHCID 14798Sodium Hydroxide

Product 1

HCID 12498110N,N-Dimethyl-N′-octylmethanimidamideYield 103.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Dimethyl sulfate (126.1 g, 1.0 mole) was heated to 65° C. The temperature was maintained at 60°-70° while dimethylformamide (73.1 g, 1.0 mole) was added over a period of about 30 minutes. After the addition was complete, the reaction was heated at 70° C. for 7 hours, then cooled to below 30° C. n-Octylamine (129.2 g, 1.0 mole) was added over a 20 minute period with external cooling to maintain the temperature at 40° C. The reaction was stirred an additional 3 hours at 40° C. after addition was complete. The reaction was cooled to about 10° C. and treated with toluene (200 ml), water (200 ml) and finally 27% sodium hydroxide solution (180 g 1.2 moles). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 190 g of a light yellow liquid which was fractionally distilled twice to yield 113 g (61%) of the title compound as a water white liquid. b.p. 115°-117° C. at 15 mm Hg.

Workup

  1. additionwas added over a period of about 30 minutes
  2. additionAfter the addition
  3. additionwas added over a 20 minute period
  4. temperaturewith external cooling
  5. temperatureto maintain the temperature at 40° C
  6. additionafter addition
  7. temperatureThe reaction was cooled to about 10° C.
  8. customThe organic phase was separated
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2ccdb057edc149df95e8d8bcf5ce04dd
Source dataset
uspto-grants-1985_02
Patent number
US04499274

Reaction notes

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