Hydrochloric Acid → 2-chloro-6-fluoro-N-hydroxybenzimidoyl chloride

HRID 434032

反応式

HRID 434032 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[CH:4]=[N:5][OH:6].[Cl:12]N1C(=O)CCC1=O.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](=[N:5][OH:6])[Cl:12]

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 31398Chlorosuccinimide2 回HCID 2755782N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine

生成物 1

HCID 713670442-chloro-6-fluoro-N-hydroxybenzimidoyl chloride収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-chloro-6-fluorobenzaldehyde oxime (5.13 g, 29.6 mmol) in DMF (50 ml) was added a portion of N-chlorosuccinimide followed by a syringe of HCl gas (5 ml from the vapors of a conc. HCl solution). The temperature increased slightly and the rest of the N-chlorosuccinimide (total of 4.07 g, 30.5 mmol) was added. After stirring at room temperature for 1 h, ice was added and the mixture was extracted twice with diethyl ether. The combined organic fractions were washed (brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexane/Et2O gradient) gave 2-chloro-6-fluorobenzoylchloride oxime (4.83 g, 78%).

後処理

  1. temperatureThe temperature increased slightly
  2. additionice was added
  3. extractionthe mixture was extracted twice with diethyl ether
  4. washThe combined organic fractions were washed (brine)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c72ccf017f6d4b39a8a8daf75103f417
出典データセット
uspto-grants-2003_12
特許番号
US06670373B1

関連ノート

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