Diethyl Ether → HCID 13557238, compound

HRID 1583480Notes

Reaction equation

HRID 1583480 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].C(N(CC)CC)C.[Cl:13][C:14]1[CH:19]=[C:18]([N:20]=[C:21]=[O:22])[CH:17]=[CH:16][C:15]=1[CH2:23][N:24]1[C:28](=[O:29])[C:27]([CH3:31])([CH3:30])[CH2:26][O:25]1.C(OCC)C>O1CCCC1>[Cl:13][C:14]1[CH:19]=[C:18]([NH:20][C:21]([N:4]([O:3][CH3:2])[CH3:5])=[O:22])[CH:17]=[CH:16][C:15]=1[CH2:23][N:24]1[C:28](=[O:29])[C:27]([CH3:31])([CH3:30])[CH2:26][O:25]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 13557270HCID 13557270, compound

Product 1

HCID 13557238HCID 13557238, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-30 °C

Procedure

A stirred solution of 2.0 grams (0.02 mole) of O,N-dimethylhydroxylamine hydrochloride in 25 ml of dry tetrahydrofuran was cooled to -30° C. and 2.0 grams (0.02 mole) of triethylamine in 25 ml of dry tetrahydrofuran was added. The reaction mixture was stirred for 20 minutes and 5.6 grams (0.02 mole) of 2-(2-chloro-4-isocyanatophenyl)methyl-4,4-dimethyl-3-isoxazolidinone in 75 ml of dry tetrahydrofuran was added dropwise. The reaction mixture temperature was maintained at -30° C. throughout the addition. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature as it stirred for 16 hours. The reaction mixture was heated under reflux for one hour then cooled to ambient temperature. The reaction mixture was placed in a separatory funnel and 20 ml of diethyl ether was added. The mixture was washed with three portions of 50 ml each of water, then dried with sodium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to a residual oil. The oil was crystallized from heptane/ethyl acetate to give 4.2 grams of 2-(2-chloro-4-[(N-methoxy-N-methylamino)carbonylamino]phenyl)methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 93°-95° C.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureto warm to ambient temperature as it
  3. stirringstirred for 16 hours
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for one hour
  6. temperaturethen cooled to ambient temperature
  7. customThe reaction mixture was placed in a separatory funnel
  8. washThe mixture was washed with three portions of 50 ml each of water
  9. dry with materialdried with sodium sulfate
  10. filtrationThe mixture was filtered
  11. concentrationthe filtrate concentrated under reduced pressure to a residual oil
  12. customThe oil was crystallized from heptane/ethyl acetate

Sources & evidence

ORD record
ord-5cd209ab77a44e779f7deb938ab2778a
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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