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

HRID 1995495

反応式

HRID 1995495 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒HCID 6342Acetonitrile溶媒2 回

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-1723d66cf886499e90e70065fbeed7c3
出典データセット
uspto-grants-1983_09
特許番号
US04405357

関連ノート

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