Dichloromethane → HCID 73794037, compound

HRID 1414848Notes

Reaction equation

HRID 1414848 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>CN(C)C=O.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 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.815 Grams of methyl methylthiomethyl sulfoxide was dissolved in 20 ml of dimethylformamide, and the solution was added with 380 mg of sodium hydride under cooling with ice, and then stirred for 1.5 hours at room temperature. Thereafter, upon addition of 1.515g of benzonitrile, the mixture was stirred for 1.5 hours at room temperature and for 10 hours at 50° C., followed by addition of 70 ml of methylene chloride and 2 ml of water and stirring for 20 minutes at room temperature. After drying with Glauber's salt and filtration, the filtrate was concentrated under reduced pressure. The resulting product was crystallized from methylene chloride-carbon tetrachloride-cyclohexane to obtain 2.332 g of 1-methylsulfinyl-1-methylthio-2-amino-2-phenylethylene. The isolation yield was 70%.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 1.5 hours at room temperature and for 10 hours at 50° C.
  3. stirringstirring for 20 minutes at room temperature
  4. dry with materialAfter drying with Glauber's salt and filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting product was crystallized from methylene chloride-carbon tetrachloride-cyclohexane

Sources & evidence

ORD record
ord-60ca8986941c46e3a13e5ab8eed02584
Source dataset
uspto-grants-1977_01
Patent number
US04002682

Reaction notes

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