Water → HCID 19594024, compound

HRID 612354Notes

Reaction equation

HRID 612354 reaction equation
[OH:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[C:10]#[N:11])[CH:5]=[CH:4]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>C1COCC1>[CH3:27][S:28]([O:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[C:10]#[N:11])[CH:5]=[CH:4]1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19594074HCID 19594074, compound

Product 1

HCID 19594024HCID 19594024, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 g (40 mmol) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-(3,4-dimethylphenyl)-acetonitrile are dissolved in 160 ml of THF and cooled in an ice bath. After adding 8.4 ml (60 mmol) of triethylamine to the solution, 3.4 ml (44 mmol) of methanesulfonyl chloride are added dropwise, keeping the temperature below 5° C. The reaction mixture is stirred in the ice bath for 30 min. The reaction mixture is poured into 150 ml of water, and extracted with ethyl acetate. The organic phase is washed with hydrochloric acid solution, water, and sodium chloride solution. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by recrystallization from toluene. 9.3 g (71%) of (4-methylsulfonyloxyiminocyclohexa-2,5-dienylidene)-(3,4-dimethylphenyl)-acetonitrile are obtained in the form of yellow crystals having a melting point of 131-133° C. (dec.).

Workup

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 5° C
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with hydrochloric acid solution, water, and sodium chloride solution
  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-8c56cc994a094ce7b8f041fcacc71f8f
Source dataset
uspto-grants-1999_12
Patent number
US06004724

Reaction notes

Loading…