Benzyl Chloride → (3-Benzyl-1,3-thiazolidin-2-ylidene)cyanamide

HRID 1086301Notes

Reaction equation

HRID 1086301 reaction equation
[H-].[Na+].[C:3]([N:5]=[C:6]1[NH:10][CH2:9][CH2:8][S:7]1)#[N:4].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[CH2:11]([N:10]1[CH2:9][CH2:8][S:7][C:6]1=[N:5][C:3]#[N:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178512079HCID 178512079, compound

Product 1

HCID 14306192(3-Benzyl-1,3-thiazolidin-2-ylidene)cyanamideYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.24 g of sodium hydride in 40 ml of N,N-dimethylformamide was added dropwise a solution of 1.27 g of 2-cyanoiminothiazolidine in 10 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. After stirring, 1.27 g of benzyl chloride was added, and the mixture was stirred at temperature for 2 hours. After the reaction, the solvent was evaporated under reduced pressure, water was added to the residue, and the resulting crystals were then collected by filtration to give 1.84 g of 3-benzyl-2-cyanoiminothiazolidine.

Workup

  1. stirringAfter stirring
  2. stirringthe mixture was stirred at temperature for 2 hours
  3. customAfter the reaction
  4. customthe solvent was evaporated under reduced pressure, water
  5. additionwas added to the residue
  6. filtrationthe resulting crystals were then collected by filtration

Sources & evidence

ORD record
ord-b0d0a3c8be6540c786b35fb57f4bae7c
Source dataset
uspto-grants-1991_07
Patent number
US05028716

Reaction notes

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