Benzylamine → (E)-2,4,6-Trimethoxystyryl 4-Methoxy-3-Nitrobenzyl sulfone

HRID 424353

反応式

HRID 424353 の反応式
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][S:8]([CH2:11][C:12](O)=O)(=[O:10])=[O:9])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18].[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[C:23]=1C=O.C(N)C1C=CC=CC=1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][S:8](/[CH:11]=[CH:12]/[C:23]2[C:26]([O:32][CH3:33])=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:22]=2[O:21][CH3:20])(=[O:10])=[O:9])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18]

参加物

5

反応物 3

HCID 7504BenzylamineHCID 700192,4,6-TrimethoxybenzaldehydeHCID 404270672-((4-Methoxy-3-nitrobenzyl)sulfonyl)acetic acid

生成物 1

HCID 11502726(E)-2,4,6-Trimethoxystyryl 4-Methoxy-3-Nitrobenzyl sulfone収率 28%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 4-methoxy-3-nitrobenzyl sulfonylacetic acid (4.5 g, 15.5 mmol) in 30 mL of glacial acetic acid was added 2,4,6-trimethoxybenzaldehyde (3.05 g, 15.5 mmol) and a catalytic amount of benzylamine (0.6 mL). The resulting mixture was heated at reflux temperature for 6 h. The reaction mixture was then concentrated under reduced pressure to yield a gummy material. The gum was triturated with 2-propanol to yield a solid product. The solid product was recrystallized from a mixture of acetic acid and 2-propanol to provide the 2-((E)-2-(4-methoxy-3-nitrobenzylsulfonyl)vinyl)-1,3,5-trimethoxybenzene product in 28% yield. m.p. 186-187° C.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature for 6 h
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customto yield a gummy material
  5. customThe gum was triturated with 2-propanol
  6. customto yield a solid product
  7. customThe solid product was recrystallized from a mixture of acetic acid and 2-propanol

出典と根拠

ORDレコード
ord-e7f2ac0ae87647c08cf8e3d13cfce0df
出典データセット
uspto-grants-2012_01
特許番号
US08106033B2

関連ノート

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