Dimethylamine → HCID 14500545, compound

HRID 2165121Notes

Reaction equation

HRID 2165121 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=1.[CH3:19][NH:20][CH3:21].O>CS(C)=O>[CH3:19][N:20]([CH3:21])[C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])=[O:18])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 579418HCID 579418, compound

Product 1

HCID 14500545HCID 14500545, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

Ten grams of N-(2,6-dimethylphenyl)-4-fluorobenzamide were dissolved in 50 ml of dimethylsulfoxide in a high pressure/temperature bomb. Anhydrous dimethylamine (18.5 g) was added and the reaction vessel sealed and heated at 150° C. for 18 hours. The bomb was cooled and the contents poured into water. The mixture was extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residue was crystallized from methanol/water affording the desired title product in 56% yield, m.p. 215°-217° C.

Workup

  1. customthe reaction vessel sealed
  2. temperatureThe bomb was cooled
  3. extractionThe mixture was extracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was crystallized from methanol/water affording the desired title product in 56% yield, m.p. 215°-217° C.

Sources & evidence

ORD record
ord-734e0e9099e342ada22ea155bda7b73f
Source dataset
uspto-grants-1990_07
Patent number
US04939163

Reaction notes

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