2-Amino-2-methyl-1-propanol → 2-{1-[4-(2-Chloro-ethyl)-phenyl]-1-methyl-ethyl}-4,4-dimethyl-4,5-dihydro-oxazole

HRID 384007Notes

Reaction equation

HRID 384007 reaction equation
C(O[C:4](=O)[C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[CH:10][CH:9]=1)([CH3:7])[CH3:6])C.[NH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21].CC(C)([O-])C.[K+].S(Cl)([Cl:32])=O.[OH-].[Na+]>C(#N)C.ClCCl>[Cl:32][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]([C:7]2[O:21][CH2:20][C:19]([CH3:23])([CH3:22])[N:18]=2)([CH3:6])[CH3:4])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 118072-Amino-2-methyl-1-propanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 23665647Potassium tert-butoxideHCID 66869809Ethyl 2-(4-(2-hydroxyethyl)phenyl)-2-methylpropanoate

Product 1

HCID 668698762-{1-[4-(2-Chloro-ethyl)-phenyl]-1-methyl-ethyl}-4,4-dimethyl-4,5-dihydro-oxazoleYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

In a reaction vessel, 2-[4-(2-hydroxy-ethyl)-phenyl]-2-methyl-propionic acid ethylester (25 g) prepared in the Example 4 and dichloromethane (200 mL) were introduced, and then 2-amino-2-methyl-1-propanol (10.6 mL) was introduced, and potassium t-butoxide (11.9 g) was slowly introduced. After the reaction was completed, distilled water (100 mL) was introduced to separate a layer, and the organic layer was condensed under reduced pressure. To the condensed organic layer, acetonitrile (150 mL) was added, and thionyl chloride (16 mL) was added dropwise, and then, the mixture was stirred to complete the reaction. After the reaction was completed, the mixture was cooled and sodium hydroxide solution was slowly added thereto to control pH from 5 to 7. Then, an organic solvent was removed by condensation, distilled water (150 mL) and dichloromethane (150 mL) were added thereto to separate layers. The separate organic layer was condensed under reduced pressure to obtain 2-{1-[4-(2-chloro-ethyl)-phenyl]-1-methyl-ethyl}-4,4-dimethyl-4,5-dihydro-oxazole (22.5 g, yield 80%).

Workup

  1. additionwere introduced
  2. distillationdistilled water (100 mL)
  3. additionwas introduced
  4. customto separate a layer
  5. customcondensed under reduced pressure
  6. customthe reaction
  7. temperaturethe mixture was cooled
  8. customThen, an organic solvent was removed by condensation
  9. distillationdistilled water (150 mL) and dichloromethane (150 mL)
  10. additionwere added
  11. customto separate layers
  12. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-c4e86c6c8696480eba69d717a279beda
Source dataset
uspto-grants-2013_02
Patent number
US08367704B2

Reaction notes

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