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

HRID 229169

反応式

HRID 229169 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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)−.

後処理

  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)

出典と根拠

ORDレコード
ord-d28c7ddfda8749a68ffbe33011d17e8d
出典データセット
uspto-grants-2009_07
特許番号
US07560589B2

関連ノート

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