Water → HCID 19077590, compound

HRID 964601Notes

Reaction equation

HRID 964601 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2/[C:16](=[N:21]\[O:22][CH3:23])/[C:17]([NH:19][CH3:20])=[O:18])[CH:5]=[CH:4][CH:3]=1.[CH3:24][S-:25].[Na+].O>O1CCCC1>[CH3:24][S:25][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2/[C:16](=[N:21]\[O:22][CH3:23])/[C:17]([NH:19][CH3:20])=[O:18])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 19077581HCID 19077581, compound

Product 1

HCID 19077590HCID 19077590, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-2-[2-(6-chloropyridin-2-yloxymethyl)phenyl]-2-methoxyimino-N-methylacetamide (1.2 g) was dissolved in tetrahydrofuran (10 ml), and sodium thiomethoxide (1 g) was added. The mixture was heated under reflux with stirring for 5 hours. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated. The resulting oil was purified by column chromatography on silica gel to give the title compound (800 mg). mp. 130°-132° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. customthe solvent was evaporated
  7. customThe resulting oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6a1f489ea28340bda4e515d0f472a66c
Source dataset
uspto-grants-1998_06
Patent number
US05770614

Reaction notes

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