Pyrrole → 4,5-Dichloro-2-(3,4-dichlorophenyl)-1-(2-hydroxyethyl)-pyrrole-2-carbonitrile

HRID 1085603노트

반응식

HRID 1085603 반응식
[Cl:1][C:2]1[C:3](C#N)=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[NH:5][C:6]=1[Cl:7].[CH3:18][C:19](C)([O-:21])C.[K+].BrC(O)C.[NH:28]1C=CC=[CH:29]1>O1CCOCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH2:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)([C:29]#[N:28])[N:5]([CH2:18][CH2:19][OH:21])[C:6]=1[Cl:7]

참가 물질

8

반응물 4

HCID 8027PyrroleHCID 1835554,5-dichloro-2-(3,4-dichlorophenyl)-1H-pyrrole-3-carbonitrileHCID 14202443Ethanol, 1-bromo-HCID 23665647Potassium tert-butoxide

생성물 1

HCID 190263774,5-Dichloro-2-(3,4-dichlorophenyl)-1-(2-hydroxyethyl)-pyrrole-2-carbonitrile

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred mixture of 2.0 g (6.5 mmol) of 4,5-dichloro-2-(3,4-dichlorophenyl)-pyrrole-3-carbonitrile and 0.88 g (7.8 mmol) of potassium tert-butoxide heated at reflux in 50 mL of dioxane is added 0.98 g (7.8 mmol) of bromoethanol. The mixture is stirred at reflux for 12 hours, cooled, diluted with 50 mL of water, and extracted several times with chloroform. The combined chloroform extracts are dried over magnesium sulfate and concentrated in vacuo to leave a solid which, on warming and dissolving in ethyl acetate, deposits on cooling mostly starting pyrrole. Concentration of the mother liquor and recrystallization of the residual solid from 20% ethyl acetate in hexane gives 0.31 g of a white solid, mp 143°-145° C.; IR 5077A.

후처리

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. temperaturecooled
  4. extractionextracted several times with chloroform
  5. dry with materialThe combined chloroform extracts are dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto leave a solid which
  8. temperatureon warming
  9. customConcentration of the mother liquor and recrystallization of the residual solid from 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-7c6a8238d4b340fea450e95059ce81ba
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05010098

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