1,1-Dichloroethane → HCID 54348717、化合物

HRID 279453

反応式

HRID 279453 の反応式
ClC(Cl)C.S(Cl)(Cl)=O.[CH3:9][C:10]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[N:24][O:25][CH3:26])[C:21]([OH:23])=O.O[N:33]=[C:34]([NH2:37])[CH2:35][CH3:36]>CCOCC.N1C=CC=CC=1.CN(C)C=O>[CH3:26][O:25][N:24]=[C:20]([C:21]1[O:23][N:37]=[C:34]([CH2:35][CH3:36])[N:33]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][O:12][C:11]1[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:10]=1[CH3:9]

参加物

8

反応物 4

HCID 63651,1-DichloroethaneHCID 24386Thionyl ChlorideHCID 4092053N-HydroxypropionimidamideHCID 54397424HCID 54397424、化合物

生成物 1

HCID 54348717HCID 54348717、化合物収率 34.5%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

Dichloroethane (5 ml), thionyl chloride (0.65 g, 5.5 mmol) and dimethylformamide (0.05 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetic acid (1.57 g, 5 mmol), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, pyridine (3 ml) and 1-hydroxyimino-l-propylamine (0.88 g, 10 mmol) were added to the residue, and the mixture was stirred under reflux for 0.5 hours. After completion of the reaction, ether (150 ml) was added, and the mixture was washed with 1N hydrochloric acid (150 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl 3-ethyl-1,2,4-oxadiazol-5-yl ketone O-methyloxime (0.63 g, 34.5%) as colorless crystals.

後処理

  1. temperatureunder reflux for 2 hours
  2. customAfter completion of the reaction
  3. additionwere added to the residue
  4. stirringthe mixture was stirred
  5. temperatureunder reflux for 0.5 hours
  6. additionwas added
  7. washthe mixture was washed with 1N hydrochloric acid (150 ml) twice
  8. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  11. customrecrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-250ef4a0f16e479a96bb861e252fb002
出典データセット
uspto-grants-2002_03
特許番号
US06362212B1

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