Water → 5-Chloromethyl-3-[4-(1-methylethyl)phenyl]-2-oxazolidinone

HRID 65688Notes

Reaction equation

HRID 65688 reaction equation
[Cl-].[Li+].[CH2:3]([CH:5]1[O:7][CH2:6]1)[Cl:4].[CH3:8][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=O)=[CH:13][CH:12]=1)[CH3:10].[OH2:20]>CN(C)C=O>[Cl:4][CH2:3][CH:5]1[O:7][C:6](=[O:20])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([CH:9]([CH3:10])[CH3:8])=[CH:12][CH:13]=2)[CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 94416p-Isopropylphenyl isocyanateHCID 433294Lithium Chloride

Product 1

HCID 227576635-Chloromethyl-3-[4-(1-methylethyl)phenyl]-2-oxazolidinoneYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

0.2-0.3 grams of lithium chloride was added to a solution of 7 grams (0.076 mole) epichlorohydrin in 30 ml dimethylformamide at 90° C. Heating was discontinued, and a solution of 12.25 grams (0.076 mole) 4(1-methylethyl)phenylisocyanate in 10 ml dimethylformamide was added dropwise at such a rate that the reaction temperature did not exceed 110° C. When the addition was complete heat was reapplied and the reaction solution was stirred at 90° C. for 3 hours. The solution was then added in a slow stream to a vigorously stirred mixture of ice and water, about 200 ml total volume. The reaction product solidified and was recovered by filtration. Recrystallization from methanol afforded an 85% yield of white crystalline material (mp 77°-79° C.).

Workup

  1. temperatureHeating
  2. customdid not exceed 110° C
  3. additionWhen the addition
  4. temperaturewas complete heat
  5. filtrationwas recovered by filtration
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-536d655f057b402093ab1f4ed21593bd
Source dataset
uspto-grants-1978_12
Patent number
US04128654

Reaction notes

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