Hydrochloric Acid → N-[4-(4-Methoxybenzoyl)phenyl]acetamide

HRID 229169

반응식

HRID 229169 반응식
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:14]1([O:20][CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH3:21][O:20][C:14]1[CH:19]=[CH:18][C:17]([C:9]([C:8]2[CH:12]=[CH:13][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)=[O:10])=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 70103414-Acetamidobenzoyl chloride

생성물 1

HCID 13499420N-[4-(4-Methoxybenzoyl)phenyl]acetamide수율 45%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A round-bottomed flask was charged with 4-acetamidobenzoyl chloride (0.95 g, 4.57 mmol), anisole (0.60 mL, 5.48 mmoL) and CH2Cl2 (15 mL). Cooled in an ice bath, AlCl3 (0.93 g, 6.85 mmol) was added in portions. The mixture was stirred at 0° C. for 4 h. The resulting dark brown solution was poured into 1 N HCl (25 mL) with ice and the mixture was extracted with EtOAc (2×60 mL). The combined EtOAc extract was washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give brown solid. The crude product was purified by chromatography on a silica gel column eluted with hexanes:EtOAc (1:1) to give 0.55 g (45%) of compound 56 as light brown solid. mp 160-162° C. 1H NMR (400 MHz, CDCl3): δ 2.22 (s, 3H), 3.88 (s, 3H), 6.96 (d, J=8.8 Hz, 2H), 7.34 (br s, 1H), 7.55-7.65 (m, 2H), 7.77 (d, J=8.6 Hz, 2H), 7.79 (d, J=8.8 Hz, 2H). LCMS (ESI): m/z 270 (M+H)+, 268 (M−H)−.

후처리

  1. temperatureCooled in an ice bath
  2. extractionthe mixture was extracted with EtOAc (2×60 mL)
  3. extractionThe combined EtOAc extract
  4. washwas washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customto give brown solid
  9. customThe crude product was purified by chromatography on a silica gel column
  10. washeluted with hexanes:EtOAc (1:1)

출처 및 근거

ORD 기록
ord-d28c7ddfda8749a68ffbe33011d17e8d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560589B2

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