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Diethyl Ether → HCID 20080506、化合物

HRID 1653822
ノート
印刷プレビュー

反応式

HRID 1653822 の反応式
C1(NC2CCCCC2)CCCCC1.[C:14]([CH:16]([CH3:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)#[N:15].S([O-])(O)(=O)=O.[Na+].C(OCC)C.Cl.[NH2:38][CH:39]([C:49]1[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=1)[C:40]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)=[O:41]>ClCCl.N1C=CC=CC=1>[Cl:48][C:45]1[CH:44]=[CH:43][C:42]([C:40](=[O:41])[CH:39]([C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[NH:38][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]([C:14]#[N:15])[CH3:25])=[CH:47][CH:46]=1
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 3283Diethyl EtherHCID 516919Sodium BisulfateHCID 20080512HCID 20080512、化合物HCID 67784761HCID 67784761、化合物

生成物 1

HCID 20080506HCID 20080506、化合物収率 80%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
20 °C

実験手順

8.2 g of 7-cyanooctanoic acid dicyclohexylamine salt are added to a mixture of 26 cm3 of a molar solution of sodium hydrogen sulphate and 60 cm3 of diethyl ether. The mixture is stirred for 15 minutes at 20° C. and the organic phase is then separated. The latter is dried over magnesium sulphate and filtered and the solvent is evaporated off under reduced pressure. The residue is treated with 13.2 g of thionyl chloride and heated to 50° C. for 3 hours. The mixture is concentrated under reduced pressure. The residual oil is dissolved in 5 cm3 of dichloromethane, and the solution obtained is added to a suspension, stirred and cooled at 5° C. of 7 g of 2-amino-1,2-bis(4-chlorophenyl)ethanone hydrochloride in 25 cm3 of dichloromethane containing 4.4 g of pyridine. After treatment, the product obtained is chromatographed on a column 2.8 cm in diameter containing 140 g of silica gel (50 to 200μ). The column is eluted with 1 liter of diisopropyl ether and then with 2.5 liters of a diisopropyl ether/ethyl acetate (90:10 by volume) mixture, collecting 250 cm3 fractions. The fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa). 7.6 g (80%) of (RS)-1,2-bis(4-chlorophenyl)-2-(7-cyanooctanamido)ethanone are obtained in the form of a yellowish oil, which is used directly in the subsequent reaction.

後処理

  1. customthe organic phase is then separated
  2. dry with materialThe latter is dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. additionThe residue is treated with 13.2 g of thionyl chloride
  6. temperatureheated to 50° C. for 3 hours
  7. concentrationThe mixture is concentrated under reduced pressure
  8. dissolutionThe residual oil is dissolved in 5 cm3 of dichloromethane
  9. customthe solution obtained
  10. additionis added to a suspension
  11. stirringstirred
  12. customAfter treatment, the product obtained
  13. customis chromatographed on a column 2.8 cm in diameter
  14. additioncontaining 140 g of silica gel (50 to 200μ)
  15. washThe column is eluted with 1 liter of diisopropyl ether
  16. customwith 2.5 liters of a diisopropyl ether/ethyl acetate (90:10 by volume) mixture, collecting 250 cm3 fractions
  17. concentrationThe fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa)

出典と根拠

ORDレコード
ord-b5d8650cf5334fbeb02e3a14d9a39a1b
出典データセット
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05403852

反応ノート

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