Thionyl Chloride → 2-(5-Bromo-2-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

HRID 1106793Notes

Reaction equation

HRID 1106793 reaction equation
S(Cl)(Cl)=O.O[CH2:6][C:7]([NH:10][C:11](=[O:21])[C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])([CH3:9])[CH3:8]>C(OCC)C>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]([C:11]2[O:21][CH2:6][C:7]([CH3:8])([CH3:9])[N:10]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22675484N-(1-hydroxy-2-methylpropan-2-yl)-5-bromo-2-methoxybenzamide

Product 1

HCID 128346732-(5-Bromo-2-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazoleYield 93.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (36.5 ml) was added dropwise to N-(1-hydroxy-2-methylpropan-2-yl)-5-bromo-2-methoxybenzamide (36.34 g). The resulting solution was stirred for 15 minutes and mixed with diethyl ether. The diethyl ether was decanted off and the resulting residue dissolved in 20% NaOH solution. The aqueous solution was extracted with diethyl ether. The extract was washed with brine, dried (MgSO4) and evaporated to give 2-(5-bromo-2-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (32.02 g).

Workup

  1. customThe diethyl ether was decanted off
  2. dissolutionthe resulting residue dissolved in 20% NaOH solution
  3. extractionThe aqueous solution was extracted with diethyl ether
  4. washThe extract was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-618064f6a1cc499782658c28fb43b4ec
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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