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

HRID 1995478

反応式

HRID 1995478 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 8058Hexane溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-0c2423f1d30746a181de50d52efac4f5
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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