Water → 3-(4,4-dimethyloxazolin-2-yl)anisole

HRID 2422402Notes

Reaction equation

HRID 2422402 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=O.O>C1COCC1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:19]2[O:11][CH2:10][C:9]([CH3:13])([CH3:12])[N:8]=2)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 74374m-Anisoyl chloride

Product 1

HCID 105601663-(4,4-dimethyloxazolin-2-yl)anisoleYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (23.0 mL) was added to a solution of 2-amino-2-methyl-1-propanol (14.4 g) in THF (200 mL), 3-methoxybenzoyl chloride (25.0 g) was dropped thereinto at 0° C. and the mixture was stirred at room temperature for 1 day. After water was added to the reaction solution, the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over sodium sulfate, filtered and concentrated in vacuo. Thionyl chloride (25 mL) was dropped into the resulting residue at 0° C. and stirred at room temperature for 3 hours. An aqueous solution of sodium hydroxide was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was evaporated in vacuo to give the aimed compound (22.0 g, 81%) as a colorless oily substance.

Workup

  1. additionwas dropped
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated saline solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThionyl chloride (25 mL) was dropped into the resulting residue at 0° C.
  8. stirringstirred at room temperature for 3 hours
  9. additionAn aqueous solution of sodium hydroxide was added to the reaction solution
  10. extractionextracted with ethyl acetate
  11. washThe organic layer was washed with a saturated saline solution
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customThe resulting residue was evaporated in vacuo

Sources & evidence

ORD record
ord-2e0ce1f966ee4c779e1b982e79db17a0
Source dataset
uspto-grants-2011_06
Patent number
US07960402B2

Reaction notes

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