Toluene → HCID 18760578, compound

HRID 1017959Notes

Reaction equation

HRID 1017959 reaction equation
[OH-].[Na+].[NH2:3][C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].C(Cl)(Cl)Cl.C(C(CC)=[O:16])C.C(N(CC)CC)C.[C:26]1([CH3:32])[CH:31]=[CH:30]C=[CH:28][CH:27]=1>>[CH2:31]([C:26]1([CH2:27][CH3:28])[C:32](=[O:16])[O:6][CH2:5][C:4]([CH3:8])([CH3:7])[NH:3]1)[CH3:30]

Participants

7

Reactant 6

HCID 1140TolueneHCID 6212ChloroformHCID 7288Ethyl ketoneHCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 18760578HCID 18760578, compound

Procedure

120 g (3 mol) of finely ground sodium hydroxide are added, with stirring, to a solution of 53.5 g (0.6 mol) of 2-amino-2-methylpropanol and 73 ml (0.9 mol) of chloroform in 635 ml (6 mol) of diethylketone at 5-10° C. The reaction mixture is stirred at room temperature for 16 hours and is then filtered. The solid is made into a slurry with 2×350 ml of methanol and filtered. The filtrates are concentrated to dryness by evaporation in a rotary evaporator and the residue is charged with 200 ml of 32% hydrochloric acid and 100 ml of water and refluxed for 6 hours. Subsequently, 600 ml of toluene are added and the water is completely removed by distillation in a water separator. 91 ml (0.66 mol) of triethylamine are then added dropwise to the toluene solution and the mixture is refluxed for another 6 hours. The precipitated triethylamine hydrochloride is removed by filtration and the filtrate is subjected to distillation at 123-127° C./20 mbar, giving compound (207) in the form of a colourless liquid, yield 63.7 g (57%).

Workup

  1. filtrationis then filtered
  2. filtrationfiltered
  3. concentrationThe filtrates are concentrated to dryness by evaporation in a rotary evaporator
  4. additionthe residue is charged with 200 ml of 32% hydrochloric acid and 100 ml of water
  5. temperaturerefluxed for 6 hours
  6. additionSubsequently, 600 ml of toluene are added
  7. customthe water is completely removed by distillation in a water separator
  8. temperaturethe mixture is refluxed for another 6 hours
  9. customThe precipitated triethylamine hydrochloride is removed by filtration
  10. distillationthe filtrate is subjected to distillation at 123-127° C./20 mbar

Sources & evidence

ORD record
ord-899e5ced7aad4c26a28762d9d4556430
Source dataset
uspto-grants-2002_11
Patent number
US06479608B1

Reaction notes

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