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

HRID 1285302
ノート
印刷プレビュー

反応式

HRID 1285302 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran
溶媒
2 回
HCID 8471Triethylamine溶媒

反応条件

温度
-5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-491fe6bf2d4e41db9feff11fd72ebfe2
出典データセット
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04567052

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート