Thionyl Chloride → Oxazole, 4,5-dihydro-4,4-dimethyl-2-phenyl-, hydrochloride

HRID 372842Notes

Reaction equation

HRID 372842 reaction equation
S(Cl)([Cl:3])=O.[C:5]([NH:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[ClH:3].[C:6]1([C:5]2[O:16][CH2:15][C:14]([CH3:18])([CH3:17])[N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 639965benzamide, N-(2-hydroxy-1,1-dimethylethyl)-

Product 1

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

Procedure

To 40 ml of freshly distilled thionyl chloride at 0° was added in portions over 15 minutes with stirring 3.86 g (0.02 mol) 2-benzoylamino-2-methyl-1-propanol. The solution was warmed to room temperature and heated under reflux for 2 hours. The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° following the addition of anhydrous ether. The solid was triturated in anhydrous ether overnight and isolated by filtration under a nitrogen atmosphere. After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%, 2-phenyl-4,4-dimethyl-1,3-oxazoline hydrochloride was obtained as a white solid, mp 149°-151°; ir (KBr) 1640 (c=N) cm-1, pmr (D2O) δ 1.60 (s, 6H), 4.70 (s, 2H) and 7.3-8.2 (m, 5H) ppm.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customThe thionyl chloride was removed under reduced pressure
  4. customto afford a yellow oil which
  5. customcrystallized at 0°
  6. additionthe addition of anhydrous ether
  7. customThe solid was triturated in anhydrous ether overnight
  8. customisolated by filtration under a nitrogen atmosphere
  9. dry with materialAfter drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%

Sources & evidence

ORD record
ord-d109789e2c4c4e62aa9d6982ec1dc21d
Source dataset
uspto-grants-1978_05
Patent number
US04092420

Reaction notes

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