Hydroxylamine → 3-chloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide

HRID 1995478

반응식

HRID 1995478 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][OH:10].N1C=CC=CC=1.[Cl:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21].NO>C(Cl)Cl.CCCCCC>[Cl:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([N:9]([CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[OH:10])=[O:21]

참가 물질

7

반응물 4

HCID 787HydroxylamineHCID 1049PyridineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 12811040N-(2-ChlorobenZyl)hydroxylamine

생성물 1

HCID 99255583-chloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide수율 20.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8058Hexane용매

실험 절차

Under an argon atmosphere a stirred solution of 10.2 grams (0.065 mole) of N-(2-chlorophenylmethyl)hydroxylamine and 6.1 grams (0.077 mole) of pyridine in 80 ml of methylene chloride was cooled to -10°. A solution of 10.0 grams (0.065 mole) of 3-chloro-2,2-dimethylpropionyl chloride in 20 ml of methylene chloride was added dropwise to the hydroxylamine solution during a 20 minute period. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it was stirred for 16 hours. The reaction mixture was diluted with 100 ml of methylene chloride and washed with 100 ml of water, 100 ml of aqueous 10% hydrochloric acid, and finally 100 ml of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a residual oil. The oil was taken up in 25 ml of hexane and cooled in an icewater bath. The resultant solid precipitate was collected by filtration and recrystallized from hexaneethyl acetate to give 3.7 grams of 3-chloro-N-(2-chlorophenyl)methyl-N-hydroxy-2,2-dimethylpropanamide; mp 108°-110°.

후처리

  1. additionUpon completion of addition the reaction mixture
  2. washwashed with 100 ml of water, 100 ml of aqueous 10% hydrochloric acid, and finally 100 ml of water
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a residual oil
  7. temperaturecooled in an icewater bath
  8. filtrationThe resultant solid precipitate was collected by filtration
  9. customrecrystallized from hexaneethyl acetate

출처 및 근거

ORD 기록
ord-0c2423f1d30746a181de50d52efac4f5
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04405357

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