1,1-Dichloroethane → HCID 54348717, 화합물

HRID 1004361

반응식

HRID 1004361 반응식
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]

참가 물질

8

반응물 4

HCID 63651,1-DichloroethaneHCID 24386Thionyl ChlorideHCID 4092053N-HydroxypropionimidamideHCID 54397424HCID 54397424, 화합물

생성물 1

HCID 54348717HCID 54348717, 화합물수율 34.5%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

Dichloroethane (5 ml), thionyl chloride (0.65 g, 5.5 mmol) and N,N-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-1-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.

후처리

  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

출처 및 근거

ORD 기록
ord-5be2124b4b6545869780796a70b63879
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048885

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