Water → 1-(Benzoyloxy)-2-methyl-2-propanaminium chloride

HRID 1764323Notes

Reaction equation

HRID 1764323 reaction equation
[ClH:1].[C:2]1([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:15]>Cl.O1CCCC1>[ClH:1].[C:8]([O:9][CH2:10][C:11]([NH2:12])([CH3:14])[CH3:13])(=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 12220134Oxazole, 4,5-dihydro-4,4-dimethyl-2-phenyl-, hydrochloride

Product 1

HCID 546091031-(Benzoyloxy)-2-methyl-2-propanaminium chloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 8.7 g (0.041 mol) 2-phenyl-4,4-dimethyl-1,3-oxazoline hydrochloride suspended in 120 ml anhydrous hydrogen chloride in tetrahydrofuran (1M) was added 3.6 ml (0.20 mol) water. The mixture was warmed to cause solution and heated under reflux with stirring for 1 hour. The tetrahydrofuran was removed under reduced pressure to afford a nearly colorless oil which crystallized at 0° following the addition of anhydrous ether. The solid was triturated with anhydrous ether overnight and isolated by filtration under a nitrogen atmosphere. After drying in vacuo over calcium sulfate, 6.9 g (0.30 mol), 73%, 2-amino-2-methyl-1-propyl benzoate hydrochloride was obtained as a white solid, mp 225°-228° (dec.) acetone:hexane, ir (KBr) 1725 (c=o) cm-1, pmr (D2O) δ 1.50 (s, 6H), 4.4 (s, 2H) and 7.0 - 8.3 (m, 5H) ppm.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureheated
  3. temperatureunder reflux
  4. customThe tetrahydrofuran was removed under reduced pressure
  5. customto afford a nearly colorless oil which
  6. customcrystallized at 0°
  7. additionthe addition of anhydrous ether
  8. customThe solid was triturated with anhydrous ether overnight
  9. customisolated by filtration under a nitrogen atmosphere
  10. dry with materialAfter drying in vacuo over calcium sulfate, 6.9 g (0.30 mol), 73%

Sources & evidence

ORD record
ord-e919bfa746e1442fa0974ddc17325e9a
Source dataset
uspto-grants-1978_09
Patent number
US04115588

Reaction notes

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