Carbamic acid, N-(4-chlorophenyl)-, ethyl ester → 3-(4-Chlorophenyl)-5-(propan-2-ylidene)-1,3-oxazolidine-2,4-dione

HRID 2289020Notes

Reaction equation

HRID 2289020 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[O:10]CC)=[CH:4][CH:3]=1.[OH:14][CH:15]([C:21]([CH3:23])=[CH2:22])[C:16]([O:18]CC)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:18])[C:15](=[C:21]([CH3:22])[CH3:23])[O:14][C:9]2=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 17496Carbamic acid, N-(4-chlorophenyl)-, ethyl esterHCID 108555893-Butenoic acid, 2-hydroxy-3-methyl-, ethyl ester

Product 1

HCID 146955623-(4-Chlorophenyl)-5-(propan-2-ylidene)-1,3-oxazolidine-2,4-dioneYield 40.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

Ethyl N-(4-chlorophenyl)carbamate (2.02 g, 10.1 mmol), ethyl 2-hydroxy-3-methyl-3-butenoate (2.97 g, 22.8 mmol) and tetrabutylammonium bromide (243 mg, 1.5 mmol) were introduced into a flask (25 cc) equipped with a distillation unit, and the reaction was conducted at 200° C. for 3.5 hours. After the reaction solution was cooled to room temperature, toluene (20 mL) was added, and then the reaction solution was washed with water (20 mL), then 1N sodium hydroxide (20 mL) and 1N hydrochloric acid (20 mL). The organic layer was dried over magnesium sulfate. After the drying agent was filtered off, the filtrate was concentrated under reduced pressure. To the resulting oily crude product, a mixed solvent consisting of methanol (5 mL) and 6N hydrochloric acid (0.25 mL) was added. The precipitated solid was collected by filtration, then washed with a 10:1 mixed solvent consisting of methanol and 6N hydrochloric acid and dried to obtain 3-(4-chlorophenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione (1.03 g, yield 40.5%).

Workup

  1. customequipped with a distillation unit
  2. washthe reaction solution was washed with water (20 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionwas added
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with a 10:1 mixed solvent
  9. customdried

Sources & evidence

ORD record
ord-b4e504b831cf4ec58f3f4d8324b387b4
Source dataset
uspto-grants-2000_07
Patent number
US06090946

Reaction notes

Loading…