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Chloral → N-[1-(Methoxyacetyloxy)-2,2,2-trichloroethyl]-3-(2,3-dichlorophenyl)-4-cyanopyrrole

HRID 1285302
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인쇄 미리보기

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HRID 1285302 반응식
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[CH:6][NH:5][CH:4]=1)#[N:2].N12CCCC=C1CCCCN2.[O:27]=[CH:28][C:29]([Cl:32])([Cl:31])[Cl:30].[CH3:33][O:34][CH2:35][C:36](Cl)=[O:37]>O1CCCC1.C(N(CC)CC)C>[CH3:33][O:34][CH2:35][C:36]([O:27][CH:28]([N:5]1[CH:4]=[C:3]([C:1]#[N:2])[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[CH:6]1)[C:29]([Cl:32])([Cl:31])[Cl:30])=[O:37]
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참가 물질

7

반응물 4

HCID 6407ChloralHCID 91724FenpiclonilHCID 96623Methoxyacetyl chlorideHCID 9834010Diazabicyclo[5.4.0]undec-7-ene

생성물 1

HCID 20248794N-[1-(Methoxyacetyloxy)-2,2,2-trichloroethyl]-3-(2,3-dichlorophenyl)-4-cyanopyrrole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran
용매
2회
HCID 8471Triethylamine용매

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온도
-5 °C

실험 절차

4.8 g of 3-cyano-4-(2,3-dichlorophenyl)pyrrole are dissolved in 50 ml of tetrahydrofuran and to the solution are added 0.2 ml of diazabicyclo[5.4.0]undec-7-ene and then 2.3 ml of chloral. The solution is cooled to -5° C., then 3.3 ml of triethylamine are added dropwise. The reaction mixture is stirred for 1 hour at -5° C. and then a solution of 2.2 ml of methoxyacetyl chloride in 10 ml of tetrahydrofuran is slowly added dropwise at -10° to -5° C. After it has been stirred for 1 hour in a thawing cooling bath, the reaction mixture is poured into ice-water and extracted twice with ethyl acetate. The organic extracts are washed twice with cold dilute hydrochloric acid and twice with a cold semi-saturated solution of sodium chloride, then dried over sodium sulfate and filtered. The filtrate is concentrated and the residue is crystallised from petroleum ether, affording colourless crystals of the title compound with a melting point of 88°-90° C.

후처리

  1. stirringAfter it has been stirred for 1 hour in a thawing
  2. temperaturecooling bath
  3. extractionextracted twice with ethyl acetate
  4. washThe organic extracts are washed twice with cold dilute hydrochloric acid and twice with a cold semi-saturated solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. customthe residue is crystallised from petroleum ether

출처 및 근거

ORD 기록
ord-491fe6bf2d4e41db9feff11fd72ebfe2
출처 데이터셋
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04567052

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