Dimethyl Sulfoxide → HCID 53843285, compound

HRID 1739657Notes

Reaction equation

HRID 1739657 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[N:14][O:15][CH3:16])[C:10]([NH:12][CH3:13])=[O:11].[H-].[Na+].[Cl:19][C:20]1[C:21]([C:30]([OH:32])=[O:31])=[N:22][C:23](S(C)(=O)=O)=[CH:24][CH:25]=1.CS(C)=O>C1COCC1.C(OCC)(=O)C.O>[CH3:16][O:15][N:14]=[C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][O:1][C:23]1[CH:24]=[CH:25][C:20]([Cl:19])=[C:21]([C:30]([O:32][C:3]([CH3:8])([CH3:4])[CH3:2])=[O:31])[N:22]=1)[C:10]([NH:12][CH3:13])=[O:11]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 218362901803604-44-5HCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Product 1

HCID 53843285HCID 53843285, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 50 mL 3-neck round bottom flask equipped with a magnetic stirring bar and N2 inlet was charged with (0.55 g, 0.0024 mol) 2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide and 10 mL anhydrous THF. To the reaction was added (0.14 g, 0.003mol) 60% NaH with stirring under nitrogen for 20 minutes. To the reaction was then added 3-chloro-6-methylsulphonylpicolinic acid: t-butyl ester (0.900 g, 0.003 mol) dissolved in 8 mL anhydrous THF, then 2 mL DMSO and stirring for three hours under nitrogen at room temperature. The mixture was then diluted with 20 mL ethyl acetate and 50 mL DI water and extracted four times with 20 mL portions of ethyl acetate. The combined organic extracts were washed three times with 50 mL portions DI water and twice with 25 mL portions brine to give the resulting product, α-(methoxyimino)-N-methyl-2-[[[5-chloro-6-(t-butoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide, as an off-white oily solid after chromatography. M.P. 103-108° C.

Workup

  1. customA 50 mL 3-neck round bottom flask equipped with a magnetic stirring bar and N2 inlet
  2. extractionextracted four times with 20 mL portions of ethyl acetate
  3. washThe combined organic extracts were washed three times with 50 mL portions DI water

Sources & evidence

ORD record
ord-6ab4c74268f34b02b0b4491d4e656559
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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