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

HRID 1741219

반응식

HRID 1741219 반응식
[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

참가 물질

9

반응물 6

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e764c100acb64ba581a7ea6e48c7a637
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05973075

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