Water → (5-Methylsulfonyloxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile

HRID 612358

Reaction equation

HRID 612358 reaction equation
[OH:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])[CH:5]=[CH:4]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C1COCC1>[CH3:24][S:25]([O:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])[CH:5]=[CH:4]1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59115159(5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile

Product 1

HCID 54441994(5-Methylsulfonyloxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrileYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g (22 mmol) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile are dissolved in 50 ml of THF and cooled in an ice bath. After adding 4.6 ml (33 mmol) of triethylamine to the solution, 1.9 ml (24 mmol) of methanesulfonyl chloride are added dropwise, keeping the temperature below 5° C. The reaction mixture is stirred while cooling in an ice bath for 30 min. The reaction mixture is poured into 200 ml of water, and extracted with ethyl acetate. The organic phase is washed with hydrochloric acid solution 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. 5.2 g (77%) of (5-Methylsulfonyloxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile are obtained in the form of greenish brown crystals having a melting point of 160-162° C. (dec.).

Workup

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 5° C
  4. temperaturewhile cooling in an ice bath for 30 min
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with hydrochloric acid solution and sodium chloride solution
  7. dry with materialThe organic phase is dried over MgSO4
  8. distillationthe solvent is distilled off
  9. customthe residue is purified by recrystallization from toluene

Sources & evidence

ORD record
ord-607654a676584d24bb1028defa5a2427
Source dataset
uspto-grants-1999_12
Patent number
US06004724

Linked notes

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