Water → HCID 54176247, compound

HRID 612360Notes

Reaction equation

HRID 612360 reaction equation
[OH:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:5]=[C:4]1[CH3:18].[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C.O>C1COCC1>[CH3:18][C:4]1[C:3](=[N:2][O:1][S:20]([CH3:19])(=[O:22])=[O:21])[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]#[N:11])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 346836HCID 346836, compound

Product 1

HCID 54176247HCID 54176247, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16.7 g (70 mmol) of crude (4-Hydroxyimino-3-methyl-cyclohexa-2,5-dienylidene)-phenylacetonitrile are dissolved in 100 ml of THF and cooled in an ice bath. After adding 6.0 ml (77 mmol) of methanesulfonyl chloride, 14.8 ml (106 mmol) of triethylamine are added dropwise to the solution, keeping the temperature below 10° C. The reaction mixture is stirred in the ice bath for 30 min., poured into 250 ml of iced water, and extracted with ethyl acetate. The organic phase is washed with 0.2 N hydrochloric acid, water, and saturated aqueous sodium chloride. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by recrystallization from toluene. 11.5 g (52%) of (3-Methyl-4-methylsulfonyloxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are obtained in the form of bright yellow crystals having a melting point of 136-138° C.(dec.).

Workup

  1. temperaturecooled in an ice bath
  2. additionare added dropwise to the solution
  3. customthe temperature below 10° C
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with 0.2 N hydrochloric acid, water, and saturated aqueous sodium chloride
  6. dry with materialThe organic phase is dried over MgSO4
  7. distillationthe solvent is distilled off
  8. customthe residue is purified by recrystallization from toluene

Sources & evidence

ORD record
ord-3903011ac176423193fe46d9e806b1ff
Source dataset
uspto-grants-1999_12
Patent number
US06004724

Reaction notes

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