N-[(4-Methoxyphenyl)methylidene]hydroxylamine → HCID 18177303, compound

HRID 610115Notes

Reaction equation

HRID 610115 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[N:8][OH:9])=[CH:5][CH:4]=1.[N:12]1([CH2:17][C:18](=[CH2:23])[C:19]([O:21]C)=[O:20])[CH:16]=[N:15][CH:14]=[N:13]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[CH2:23][C:18]([C:19]([OH:21])=[O:20])([CH2:17][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[O:9][N:8]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 94712N-[(4-Methoxyphenyl)methylidene]hydroxylamineHCID 18177257HCID 18177257, compound

Product 1

HCID 18177303HCID 18177303, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxybenzaldehyde oxime (1.63, g, 10.8 mmol) and methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate.(1.50 g, 8.97 mol) were added together with 100 mL of CH2Cl2. To the above mixture was added bleach (23 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The mixture was diluted with CH2Cl2 and washed with water and brine, It was dried over MgSO4, concentrated, and chromatographed with 30-100% EtOAc in CH2Cl2 on silica gel to give 1.81 g of the desired product (66%).

Workup

  1. washwashed with water and brine, It
  2. dry with materialwas dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed with 30-100% EtOAc in CH2Cl2 on silica gel

Sources & evidence

ORD record
ord-a1bbce443b6a481a8131dec6b8bf9fa6
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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