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

HRID 434032

반응식

HRID 434032 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 31398Chlorosuccinimide2회HCID 2755782N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine

생성물 1

HCID 713670442-chloro-6-fluoro-N-hydroxybenzimidoyl chloride수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c72ccf017f6d4b39a8a8daf75103f417
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670373B1

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