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Water → methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-[1-(N-methoxyimino)ethyl]benzoate

HRID 4903
Notes
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Reaction equation

HRID 4903 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([S:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=O)[CH3:23])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[N:4]=1.Cl.[CH3:26][O:27][NH2:28].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([S:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[N:28][O:27][CH3:26])[CH3:23])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 19089402Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoate

Product 1

HCID 86747183methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-[1-(N-methoxyimino)ethyl]benzoateYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoate and 0.5 g of methoxyamine hydrochloride were dissolved in 6 ml of methanol, and the resultant solution was refluxed for 15 minutes. After cooling the mixed liquor to room temperature, 0.8 g of potassium carbonate was added to this liquor and the resultant liquor was heat-refluxed for 3 hours. The reaction liquor was poured into a large amount of water, and an oily product thus precipitated was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and was dried to distill off ethyl acetate under reduced pressure. The residue thus obtained was purified by chromatography to obtain 0.65 g of the aimed compound (refractive index=1.5709) at a yield of 59%.

Workup

  1. temperaturethe resultant liquor was heat-refluxed for 3 hours
  2. customan oily product thus precipitated
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. customwas dried
  6. distillationto distill off ethyl acetate under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by chromatography

Sources & evidence

ORD record
ord-a7a4e504e0e84b019b4a1e1fa710be55
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