Potassium Carbonate → 2-[(2-Chloro-6-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one

HRID 1995495

반응식

HRID 1995495 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1([CH3:14])[CH2:12][O:11][NH:10][C:9]1=[O:13].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[CH2:23]Cl>C(#N)C.O1CCOCCOCCOCCOCCOCC1>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[CH2:23][N:10]1[C:9](=[O:13])[C:8]([CH3:14])([CH3:7])[CH2:12][O:11]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 6421514,4-Dimethyl-1,2-oxazolidin-3-one

생성물 1

HCID 131925712-[(2-Chloro-6-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one수율 46.6%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6342Acetonitrile용매2회

실험 절차

To a stirred suspension of 3.6 grams (0.026 mole) of potassium carbonate and 0.14 gram (0.0005 mole) of 1,4,7,10,13,16-hexaoxacyclooctadecane in 50 ml of acetonitrile was added dropwise a solution of 3.0 grams (0.026 mole) of 4,4-dimethyl-3-isoxazolidinone (Example 30, Step B) and 4.7 grams (0.025 mole) of (2-chloro-6-fluorophenyl)methyl chloride in 25 ml of acetonitrile. The complete addition required 30 minutes. Upon completion of addition the reaction mixture was stirred at ambient temperature for 18 hours, and then filtered. The filtrate was diluted with 200 ml of methylene chloride and washed with three 100-ml portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give an oil residue. The oil solidified and was recrystallized from petroleum ether to give 3.0 grams of 2-[(2-chloro-6-fluorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone; mp 49°-51°.

후처리

  1. additionThe complete addition required 30 minutes
  2. additionUpon completion of addition the reaction mixture
  3. filtrationfiltered
  4. additionThe filtrate was diluted with 200 ml of methylene chloride
  5. washwashed with three 100-ml portions of water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give an oil residue
  10. customwas recrystallized from petroleum ether

출처 및 근거

ORD 기록
ord-1723d66cf886499e90e70065fbeed7c3
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04405357

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