Potassium Carbonate → HCID 13557217, compound

HRID 1583476Notes

Reaction equation

HRID 1583476 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1([CH3:14])[CH2:12][O:11][NH:10][C:9]1=[O:13].[CH3:15][O:16][C:17](=[O:28])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[C:21]([Cl:27])[CH:20]=1>C(#N)C.O1CCOCCOCCOCCOCCOCC1>[Cl:27][C:21]1[CH:20]=[C:19]([NH:18][C:17]([O:16][CH3:15])=[O:28])[CH:24]=[CH:23][C:22]=1[CH2:25][N:10]1[C:9](=[O:13])[C:8]([CH3:14])([CH3:7])[CH2:12][O:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6421514,4-Dimethyl-1,2-oxazolidin-3-oneHCID 13557216HCID 13557216, compound

Product 1

HCID 13557217HCID 13557217, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred suspension of 2.4 grams (0.017 mole) of potassium carbonate and 0.1 gram (0.02 eq.) of 1,4,7,10,13,16-hexaoxacyclooctadecane in 60 ml of acetonitrile, at ambient temperature, was added dropwise a mixture of 2.0 grams (0.017 mole) of 4,4-dimethyl-3-isoxazolidinone and 4.8 grams (0.017 mole) of methyl(4-bromomethyl-3-chlorophenyl)carbamate in 30 ml of acetonitrile. The complete addition required 30 minutes, after which the reaction mixture stirred for 16 hours. The reaction mixture was filtered to collect a solid. The solid was slurried with 300 ml of water and the insoluble material collected by filtration. The filter cake was recrystallized from hexane/ethyl acetate to give 2.4 grams of 2-[2-chloro-4-(methyloxycarbonylamino)phenyl]methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 165°-167° C. (Compound 14)

Workup

  1. additionat ambient temperature, was added dropwise
  2. additionThe complete addition required 30 minutes
  3. filtrationThe reaction mixture was filtered
  4. customto collect a solid
  5. filtrationthe insoluble material collected by filtration
  6. customThe filter cake was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-74dd4ae4b8384d8d90fe1e04e1355300
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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