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

HRID 2361270노트

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HRID 2361270 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c483b49dd074fb58f92a9c677250014
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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