Dimethyl Sulfoxide → HCID 12834316, compound

HRID 1065260Notes

Reaction equation

HRID 1065260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:11](=[O:23])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:24]S(C)=O.[H-].[Na+].IC>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:11](=[O:23])[N:10]([CH3:24])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12834315Ethyl 1-(4-fluorophenyl)-4-hydroxy-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate

Product 1

HCID 12834316HCID 12834316, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred and cooled (below 5° C.) mixture of 16 parts of ethyl 1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]decane-8-carboxylate, 200 parts of dimethyl sulfoxide and 200 parts of benzene are added 3.5 parts of a sodium hydride dispersion 50%. After stirring for 1 hour at a temperature below 5° C., there are added dropwise 10 parts of iodomethane at this temperature. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto water and the layers are separated. The aqueous phase is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated, yielding 14.7 parts (88%) of ethyl 1-(4-fluorophenyl)-3-methyl-4-oxo-1,3,8-triazaspiro[4,5]decane-8-carboxylate as a residue.

Workup

  1. temperaturecooled
  2. stirringAfter stirring for 1 hour at a temperature below 5° C., there
  3. stirringUpon completion, stirring
  4. additionThe reaction mixture is poured onto water
  5. customthe layers are separated
  6. extractionThe aqueous phase is extracted with methylbenzene
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-c3e3168f22204290b3c4177bb3841a8c
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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