2-Amino-2-methyl-1-propanol → 4,5-Dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazole

HRID 484473Notes

Reaction equation

HRID 484473 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](Cl)=O)=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>ClCCl>[CH3:5][C:2]1([CH3:6])[CH2:3][O:4][C:19]([C:18]2[CH:22]=[CH:23][C:15]([O:14][CH2:13][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:16][CH:17]=2)=[N:1]1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 149891694,5-Dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazoleYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (0° C.) mixture of 4.5 parts of 2-amino-2-methyl-1-propanol and 180 parts of dichloromethane were added portionwise 4.93 parts of 4-(phenylmethoxy) benzoyl chloride. Upon complete addition, stirring was continued for 48 hours at room temperature. The precipitate was filtered off and the filtrate was evaporated. The residue was stirred in 2,2'-oxybispropane. The precipitated product was filtered off and stirred in 9.6 parts of thionyl chloride during 1 hour. After evaporation, the residue was taken up in a sodium hydroxide solution 10%, crushed ice and methylbenzene. The separated organic layer was washed with water, dried, filtered and evaporated, yielding 5 parts (90%) of 4,5-dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazole as a residue (int. 1).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. filtrationThe precipitate was filtered off
  5. customthe filtrate was evaporated
  6. stirringThe residue was stirred in 2,2'-oxybispropane
  7. filtrationThe precipitated product was filtered off
  8. stirringstirred in 9.6 parts of thionyl chloride during 1 hour
  9. customAfter evaporation
  10. customcrushed ice and methylbenzene
  11. washThe separated organic layer was washed with water
  12. customdried
  13. filtrationfiltered
  14. customevaporated

Sources & evidence

ORD record
ord-0bb383eccda54ab0baf544e00b1f00f1
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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