Hydrochloric Acid → 1-(4-Chlorophenyl)-3-(dimethylamino)propan-1-one

HRID 1741219

反応式

HRID 1741219 の反応式
[H][H].Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:17])[CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[CH:7][CH:6]=1.CC(C1C=CC(Cl)=CC=1)=O.Cl.CNC.C=O.Cl>C(O)C.CC(C)=O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:17])[CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[CH:9][CH:10]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7467P-ChloroacetophenoneHCID 10473Dimethylamine, hydrochlorideHCID 2003701-Propanone, 1-(4-chlorophenyl)-3-(dimethylamino)-, hydrochloride (1:1)HCID 178418361HCID 178418361、化合物

生成物 1

HCID 2003711-(4-Chlorophenyl)-3-(dimethylamino)propan-1-one

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 702Ethanol溶媒

実験手順

The procedure of Example 13 is followed, but the endcapper is 4'-chloro-3-dimethylaminopropiophenone (0.10 g, 0.47 mmol) to yield the ketone-functionalized macromonomer. The product has structure 1, where G1 is benzoyl, G2 through G4 are hydrogen, E is 4'-(3-dimethyl-aminopropionyl)phenyl, and DPn ≈28. This oligomer can be converted to the more useful acrylyl-terminated form by thermally induced loss of dimethylamine. 4'-Chloro-3-dimethylaminopropiophenone is prepared by treating 4'-chloro-3-dimethylaminopropiophenone hydrochloride with aqueous base to remove the HCl. The free amine is extracted into diethyl ether and recovered by evaporation of the solvent. The hydrochloride salt is prepared by the method of Maxwell in Org. Synth. Coll. Vol. III, 305-306. Thus, a mixture of 4-chloroacetophenone, dimethylamine hydrochloride, and paraformaldehyde is refluxed for 2-4 hours in 95% ethanol with a small amount of added hydrochloric acid. The solid product is obtained after adding acetone and cooling overnight.

後処理

  1. customterminated form by thermally induced loss of dimethylamine
  2. customto remove the HCl
  3. extractionThe free amine is extracted into diethyl ether
  4. customrecovered by evaporation of the solvent
  5. customThe solid product is obtained
  6. temperaturecooling overnight

出典と根拠

ORDレコード
ord-e764c100acb64ba581a7ea6e48c7a637
出典データセット
uspto-grants-1999_10
特許番号
US05973075

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