Water → HCID 178418326, compound

HRID 3237Notes

Reaction equation

HRID 3237 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[S:7])[NH:4][C:3]1=[O:8].Cl.[CH3:11][N:12]([CH3:21])[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl.O.[OH-].[Na+]>CS(C)=O>[CH3:11][N:12]([CH3:21])[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][S:7][C:5]1[NH:6][C:2]([CH3:9])([CH3:1])[C:3](=[O:8])[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 30021405,5-Dimethyl-2-sulfanylideneimidazolidin-4-oneHCID 135374262-(chloromethyl)-N,N-dimethylaniline hydrochloride

Product 1

HCID 178418326HCID 178418326, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Initially, 1 g of 5,5-dimethyl-2-thiohydantoin was dissolved in 20 mL of dimethylsulfoxide, and 1.7 g of 2-dimethylaminobenzylchloride hydrochloride was added to the solution. The reaction mixture was stirred at the room temperature for one hour, and poured into 50 mL of water. The pH value of the solution was adjusted to 7-8 with diluted aqueous solution of 2N sodium hydroxide (NaOH). A precipitated sediment was extracted from the liquid, two times, using 50 mL of ethyl acetate (AcOEt). The AcOEt layer was successively washed with 50 mL of water and 50 mL of brine, dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The thus obtained residue was purified by column chromatography [developing solvent=CHCl3 :MeOH=20:1 (volume ratio, v/v)]. Recrystallized from diethyl ether gave the desired compound in the form of needle-like crystal. The yield of the compound was 1.2 g with a yield ratio of 62.4%, and its melting point was 113°-115° C.

Workup

  1. extractionA precipitated sediment was extracted from the liquid, two times
  2. washThe AcOEt layer was successively washed with 50 mL of water and 50 mL of brine
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe thus obtained residue was purified by column chromatography [developing solvent=CHCl3 :MeOH=20:1 (volume ratio, v/v)]
  6. customRecrystallized from diethyl ether

Sources & evidence

ORD record
ord-f1dc421f62bb4c91b491d7738aa0887d
Source dataset
uspto-grants-1998_03
Patent number
US05733922

Reaction notes

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