Dimethyl Sulfate → HCID 12557677, compound

HRID 1438888Notes

Reaction equation

HRID 1438888 reaction equation
[OH:1][C:2]1[C:3](=[O:20])[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[C:21](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(=O)CC>[CH3:21][O:20][C:3]1[C:2](=[O:1])[C:8]([NH:9][S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 12557675HCID 12557675, compound

Product 1

HCID 12557677HCID 12557677, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-hydroxy-3-[N-[(4-methylphenyl)sulfonyl]-amino]-2,4,6-cycloheptatrien-1-one (14.5 g), potassium carbonate (12.5 g), dimethyl sulfate (12.5 g) and 2-butanone (145 ml) is heated at reflux for 1 hour. The mixture is filtered and the precipitate is washed with water and suspended in ethyl actate. Hydrochloric acid (10%) is added until the solution is acidic. The organic phase is collected and dried over sodium sulfate. Evaporation of the solvent and crystallization of the residue from ethyl acetate-hexane gives 2-methoxy-7-[N-[(4-methylphenyl)sulfonyl]amino]-2,4,6-cycloheptatrien-1-one, mp 163°-164° C. The above filtrate is evaporated and the residue is subjected to chromatography on silica gel using ethyl acetate-hexane (3:1). Evaporation of the eluates are crystallization of the residue from ethyl acetate gives 2-methoxy-3-[N-[(4-methylphenyl)sulfonyl]-N-methylamino]-2,4,6-cycloheptatrien-1-one, mp 101°-102° C and 2-methoxy-7-[N-[(4-methylphenyl)sulfonyl]-N-methylamino]-2,4,6-cycloheptatrien-1-one, mp 94.5° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe mixture is filtered
  4. washthe precipitate is washed with water
  5. additionHydrochloric acid (10%) is added until the solution
  6. customThe organic phase is collected
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the solvent and crystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9a236378cb6149b59f45e2cba44aaf77
Source dataset
uspto-grants-1977_11
Patent number
US04057556

Reaction notes

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