Dichloromethane → HCID 73794037, compound

HRID 1606253Notes

Reaction equation

HRID 1606253 reaction equation
[CH3:1][S:2][CH2:3][S:4]([CH3:6])=[O:5].[H-].[Na+].[C:9](#[N:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(Cl)Cl>C1COCC1.O>[CH3:6][S:4]([C:3]([S:2][CH3:1])=[C:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7505BenzonitrileHCID 24758Sodium hydrideHCID 99129Methyl (methylsulfinyl)methyl sulfide

Product 1

HCID 73794037HCID 73794037, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.38 Grams of methyl methylthiomethyl sulfoxide was dissolved in 45 ml of THF, and to the solution 900 mg of sodium hydride was added under cooling with ice, and the system was stirred for an hour at room temperature. Upon addition of 4 ml of benzonitrile and subsequent stirring for 42.5 hours at room temperature, the entire system was solidified, to which 100 ml of methylene chloride and 3 ml of water were added, followed by 30 minutes' stirring and then drying with Glauber's salt. The light yellow solid obtained by the subsequent concentration under reduced pressure was washed with 100 ml of carbon tetrachloride, and 5.158 g of 1-methylsulfinyl-1-methylthio-2-amino-2-phenylethylene was obtained as a light yellow solid. The washing was concentrated under reduced pressure, and subjected to a column chromatography (silica gel, ethyl acetate, and methanol) to allow the recovery of 1.106 g of a light yellow, oily substance. Upon NMR analysis, the oily substance was confirmed to be composed of 972 mg of methyl methylthiomethyl sulfoxide and 134 mg of 1-methylsulfinyl-1-methylthio-2-amino-2-phenylethylene. The latter's isolation yield was 66%, and the conversion yield was 84.8%.

Workup

  1. temperatureunder cooling with ice
  2. stirringsubsequent stirring for 42.5 hours at room temperature
  3. additionwere added
  4. stirring' stirring
  5. dry with materialdrying with Glauber's salt
  6. customThe light yellow solid obtained by the subsequent concentration under reduced pressure
  7. washwas washed with 100 ml of carbon tetrachloride

Sources & evidence

ORD record
ord-6e41fb6521d84d2680dae041035a7766
Source dataset
uspto-grants-1976_04
Patent number
US03952044

Reaction notes

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