Hydrogen Bromide → (2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 1756739Notes

Reaction equation

HRID 1756739 reaction equation
[CH3:1][NH:2][C:3](=[O:21])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:5]\[O:6][CH3:7].Br.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3](=[O:21])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[N:5]/[O:6][CH3:7]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 9576038(Z)-Metominostrobin

Product 1

HCID 5483872(2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(Z)-N-Methyl-2-(2-phenoxyphenyl)-2-methoxyiminoacetamide (570 mg, 2 mmol) was dissolved in toluene (10 ml). Hydrobromic acid (47%, 0.52 g) was addd, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, a saturated aqueous solution of sodium bicarbonate (50 ml) was added for neutralization. The resulting mixture was extracted with methylene chloride (130 ml), washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (E)-N-methyl-2-(2-phenoxyphenyl)-2-methoxyiminoacetamide (564 mg, Yield: 98.9%, E/Z=96/4).

Workup

  1. customAfter completion of the reaction
  2. extractionThe resulting mixture was extracted with methylene chloride (130 ml)
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a765ab1990347818484e232a879970e
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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