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

HRID 2361270Notes

Reaction equation

HRID 2361270 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9c483b49dd074fb58f92a9c677250014
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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