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Methanol → methyl 2-[(4,6-dimethoxytriazin-2-y1)oxy]-6-[1-(N-methoxyimino)ethyl]benzoate

HRID 4908
Notes
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Reaction equation

HRID 4908 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][N:15]2[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[NH:16]2)[C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=O)[CH3:2].Cl.[CH3:26][O:27][NH2:28].C([O-])(=O)C.[K+].CO>O>[CH3:22][O:21][C:19]1[CH:18]=[C:17]([O:23][CH3:24])[NH:16][N:15]([O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:1](=[N:28][O:27][CH3:26])[CH3:2])[C:5]=2[C:6]([O:8][CH3:9])=[O:7])[N:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 517044Potassium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 19089388Methyl 2-acetyl-6-[(4,6-dimethoxytriazin-2-yl)oxy]benzoate

Product 1

HCID 86747186methyl 2-[(4,6-dimethoxytriazin-2-y1)oxy]-6-[1-(N-methoxyimino)ethyl]benzoateYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.9 of methyl 2-acetyl-6-[(4,6-dimethoxytriazin-2-yl)oxy]benzoate, 0.68 g of methoxyamine hydrochloride and 0.80 g of potassium acetate were added to 30 ml of methanol, and the resultant mixture was stirred for one day and one night at room temperature. The resultant reaction liquor was poured into water, and was extracted with ethyl acetate. After washing the extracted product with water, the washed product was dried and concentrated to obtain an oily product. This was then purified by column chromatography to obtain 0.47 g of the aimed compound (melting point=131° to 135° C.) at a yield of 48%.

Workup

  1. customThe resultant reaction liquor
  2. extractionwas extracted with ethyl acetate
  3. washAfter washing the extracted product with water
  4. customthe washed product was dried
  5. concentrationconcentrated
  6. customto obtain an oily product
  7. customThis was then purified by column chromatography

Sources & evidence

ORD record
ord-9caf7f2af9b04e69903afed00c9e43d0
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05242895

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes