Triethylamine → HCID 13557232, compound

HRID 1583482Notes

Reaction equation

HRID 1583482 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[C:4]([Cl:17])[CH:3]=1.C(N(CC)CC)C.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>O1CCCC1>[Cl:17][C:4]1[CH:3]=[C:2]([NH:1][C:28]([CH:25]2[CH2:27][CH2:26]2)=[O:29])[CH:7]=[CH:6][C:5]=1[CH2:8][N:9]1[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[CH2:11][O:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 13557219HCID 13557219, compound

Product 1

HCID 13557232HCID 13557232, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3.0 grams (0.012 mole) of 2-(4-amino-2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and 1.2 grams (0.012 mole) of triethylamine in 30 ml of tetrahydrofuran was added dropwise 1.4 grams (0.013 mole) of cyclopropanecarboxylic acid chloride in 20 ml of tetrahydrofuran. During the addition the reaction mixture was cooled in an ice-water bath. Upon completion of addition the reaction mixture stirred for 16 hours; then was concentrated under reduced pressure to a residual solid. The solid was dissolved in 250 ml of methylene chloride. The solid was washed with water, which caused the precipitation of a solid that was insoluble in the liquid phases. The solid was removed by filtration. The organic phase was separated and washed with three 100 ml portions of water. The organic phase was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual solid. Both solids collected were subjected to thin layer chromatography and were determined to be the same material. The solids were combined and recrystallized from ethyl acetate/acetonitrile to give 2.5 grams of 2-[2-chloro-4-(cyclopropylcarbonylamino)phenyl]methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 191°-193° C.

Workup

  1. additionDuring the addition the reaction mixture
  2. temperaturewas cooled in an ice-water bath
  3. additionUpon completion of addition the reaction mixture
  4. concentrationthen was concentrated under reduced pressure to a residual solid
  5. dissolutionThe solid was dissolved in 250 ml of methylene chloride
  6. washThe solid was washed with water, which
  7. customthe precipitation of a solid
  8. customThe solid was removed by filtration
  9. customThe organic phase was separated
  10. washwashed with three 100 ml portions of water
  11. dry with materialThe organic phase was dried with magnesium sulfate
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated under reduced pressure to a residual solid
  14. customBoth solids collected
  15. customrecrystallized from ethyl acetate/acetonitrile

Sources & evidence

ORD record
ord-7931df10fac748ef84914c71b0262951
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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