Sodium Methoxide → HCID 178461661, compound

HRID 850091Notes

Reaction equation

HRID 850091 reaction equation
C[N:2]([C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:31])[C:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])([OH:22])[CH2:16][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[CH:10][CH:9]=1)[NH:3][C:4]([NH2:6])=[S:5].[CH3:33][O-].[Na+]>C(O)C>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[C@:15]([OH:22])([C@H:14]([C:11]1[CH:10]=[CH:9][C:8]([C:7]2[N:6]([CH3:33])[C:4]([SH:5])=[N:3][N:2]=2)=[CH:13][CH:12]=1)[CH3:31])[CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 88121525HCID 88121525, compound

Product 1

HCID 178461661HCID 178461661, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-methyl-4-{2-[2,4-difluorophenyl]-2-hydroxy-1-[1,2,4-triazol-1-yl]but-3-yl}benzoylthiosemicarbazide (2.1 g, 4.5 mmol) in ethanol (50 ml) was heated under reflux and treated with sodium methoxide solution (30%, 5.5 mmol) in portions over 24 hours. The mixture was reduced in volume to 20 ml under reduced pressure and partitioned between ethyl acetate (100 ml) and water (50 ml). The aqueous layer was further extracted with ethyl acetate (3×50 ml) and the organic extracts combined, washed with brine (50 ml), dried (Na2SO4) and evaporated under reduced pressure.

Workup

  1. temperatureunder reflux
  2. custompartitioned between ethyl acetate (100 ml) and water (50 ml)
  3. extractionThe aqueous layer was further extracted with ethyl acetate (3×50 ml)
  4. washwashed with brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a06cc584a9314e42a035a1b2b9746cc1
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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