Dimethylformamide → HCID 54186607, compound

HRID 1395556Notes

Reaction equation

HRID 1395556 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].CN(C=O)C.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([O:4][CH2:3][CH2:2][N:1]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5][CH2:6][O:7][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 8113DiethanolamineHCID 24758Sodium hydride2×

Product 1

HCID 54186607HCID 54186607, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethanolamine (42.0 g., 0.4 mole) is stirred under nitrogen in 800 ml. of dry DMF at 0° C. and 50% NaH in mineral oil (57.6 g., 1.2 mole) is added in small portions. After the sodium hydride has reacted, benzyl bromide (205.3 g., 1.2 mole) is added dropwise. The mixture is allowed to come to room temperature while stirring overnight. The reaction mixture is poured into water and is extracted with ether. The ether solution is extracted with dilute HCl. The acid extract is basified with NaOH and extracted with ether. Crude product is recovered by drying, filtering and evaporating the ether. The residual liquid (138.4 g.) is subjected to distillation at 290° C. and 0.01 mm. to remove volatile impurities. This gives 114.4 g. of amber oil.

Workup

  1. customto come to room temperature
  2. extractionis extracted with ether
  3. extractionThe ether solution is extracted with dilute HCl
  4. extractionThe acid extract
  5. extractionextracted with ether
  6. customCrude product is recovered
  7. customby drying
  8. filtrationfiltering
  9. customevaporating the ether
  10. distillationThe residual liquid (138.4 g.) is subjected to distillation at 290° C.
  11. customto remove volatile impurities

Sources & evidence

ORD record
ord-79c22fd5e48f43caa4ba7528d5ec0077
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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