Dimethylformamide dimethyl acetal → 3-Dimethylamino-1-(2'-methoxy-5'-acetamidophenyl)prop-2-en-1-one

HRID 1159494노트

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HRID 1159494 반응식
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22]>C(O)C>[CH3:6][N:4]([CH3:5])[CH:3]=[CH:22][C:21]([C:12]1[CH:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[CH:15]=[CH:16][C:11]=1[O:10][CH3:9])=[O:23]

참가 물질

4

반응물 2

HCID 78373Dimethylformamide dimethyl acetal3회HCID 28174183-Acetyl-4-methoxyacetanilide

생성물 1

HCID 666034303-Dimethylamino-1-(2'-methoxy-5'-acetamidophenyl)prop-2-en-1-one수율 101.4%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
22 °C

실험 절차

Dimethylformamide dimethyl acetal (693.3 g) was added to a suspension of 2′-methoxy-5′-acetamidoacetophenone (3, 1215.1 g) in ethanol (12.15 L) stirred under nitrogen at 22° C. After the resulting suspension had been stirred and refluxed under nitrogen for 18 hours, all solids had dissolved, and additional dimethylformamide dimethyl acetal (346.2 g) was added to the homogeneous reaction mixture. Stirring and refluxing under nitrogen were continued for an additional 30 hours, after which additional dimethylformamide dimethyl acetal (346.2 g) was added. The reaction mixture was then stirred and refluxed under nitrogen for a final 17.5 hours, after which the reaction mixture was rotary evaporated at <45° C. and <50 mm HgA to a solid residue that was dried further overnight at <45° C. and <1 mm HgA to provide brown solid 4 (1547.9 g, 100.6% yield). LC/MS analyses revealed 98.3% and 100% conversion of 3 to 4 before and after evaporation of solvent, respectively.

후처리

  1. stirringAfter the resulting suspension had been stirred
  2. temperaturerefluxed under nitrogen for 18 hours
  3. dissolutionall solids had dissolved
  4. stirringStirring
  5. temperaturerefluxing under nitrogen
  6. stirringThe reaction mixture was then stirred
  7. temperaturerefluxed under nitrogen for a final 17.5 hours
  8. customafter which the reaction mixture was rotary evaporated at <45° C.
  9. custom<50 mm HgA to a solid residue that was dried further overnight at <45° C.

출처 및 근거

ORD 기록
ord-662f99a291d04c5db5a170b694992c61
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812176B2

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