Acetic Acid → (E)-Benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate

HRID 2361270ノート

反応式

HRID 2361270 の反応式
[CH:1]([C:3]1[C:4]([CH3:20])=[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1)=O.[N+:21]([CH3:24])([O-:23])=[O:22].C([O-])(=O)C.[NH4+].C(O)(=O)C>>[CH3:20][C:4]1[C:3](/[CH:1]=[CH:24]/[N+:21]([O-:23])=[O:22])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 86681516Benzyl 3-formyl-2-methylphenylcarbamate

生成物 1

HCID 67995173(E)-Benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate収率 71.7%

反応条件

温度
90 °C

実験手順

A mixture of benzyl 3-formyl-2-methylphenylcarbamate (4.968 g, 18.45 mmol), nitromethane (2.478 mL, 46.1 mmol), and ammonium acetate (3.56 g, 46.1 mmol) in acetic acid (70 mL, 1223 mmol) was heated at 90° C. for 4.5 hr. The acetic acid was removed under vacuum. To the residue was added water (100 mL), and the mixture was stirred at room temperature for 30 min. The insoluble material was collected with suction filtration. The filter cake was mixed with water (100 mL) and the aqueous mixture was adjusted to pH 9 with saturated NaHCO3 solution and stirred at room temperature for 30 min. The insoluble product (4.13 g, 88% purity, 13.22 mmol, 71.7% yield) was collected as a yellow solid with suction filtration and dried over Drierite under vacuum.

後処理

  1. customThe acetic acid was removed under vacuum
  2. additionTo the residue was added water (100 mL)
  3. filtrationThe insoluble material was collected with suction filtration
  4. additionThe filter cake was mixed with water (100 mL)
  5. stirringstirred at room temperature for 30 min
  6. filtrationThe insoluble product (4.13 g, 88% purity, 13.22 mmol, 71.7% yield) was collected as a yellow solid with suction filtration
  7. dry with materialdried over Drierite under vacuum

出典と根拠

ORDレコード
ord-9c483b49dd074fb58f92a9c677250014
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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