Hydrochloric Acid → HCID 178459973, compound

HRID 1638837Notes

Reaction equation

HRID 1638837 reaction equation
[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][NH:5]1)#[N:2].[H-].[Na+].[H][H].[C:13](Cl)(=[O:16])[CH2:14][CH3:15].Cl>CN(C)C=O.ClCCl>[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][N:5]1[C:13](=[O:16])[CH2:14][CH3:15])#[N:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 62324Propionyl chlorideHCID 178418361HCID 178418361, compoundHCID 178512073HCID 178512073, compound

Product 1

HCID 178459973HCID 178459973, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2.2 g of 2-cyanoimino-imidazolidine is dissolved in 20 ml of dry dimethyl formamide. To this solution were portionwise added 1.7 g of 60% oil dispersed sodium hydride at a temperature of at most 0° C. The reaction mixture was stirred at 0° C. until the evolution of hydrogen had ceased. To the reaction mixture were dropwise added 1.9 g of propionyl chloride while the reaction mixture was kept at a temperature lower than 0° C. After this addition, the reaction mixture was stirred at room temperature for a short period of time. The reaction mixture was poured into ice water, and neutralized with hydrochloric acid. An extraction operation was carried out by using dichloromethane, and the extractant was concentrated, so that the aimed product was precipitated as a crystalline material. The precipitated product was separated by filtration, and washed in ether, 1.4 g of 2-cyanoimino-1-propionyl-imidazolidine were obtained. mp. 208°-210° C.

Workup

  1. customwas kept at a temperature lower than 0° C
  2. additionAfter this addition
  3. concentrationthe extractant was concentrated, so that the aimed product
  4. customwas precipitated as a crystalline material
  5. customThe precipitated product was separated by filtration
  6. washwashed in ether

Sources & evidence

ORD record
ord-295f61e414d343a3868b1bb685195fa3
Source dataset
uspto-grants-1989_11
Patent number
US04880933

Reaction notes

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