Acetamidine monohydrochloride → HCID 178433486, compound

HRID 718223Notes

Reaction equation

HRID 718223 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[F:6][C:7]1[CH:24]=[CH:23][C:10]([C:11]([NH:13][CH:14]([C:19](OC)=[O:20])[C:15](OC)=[O:16])=[O:12])=[CH:9][CH:8]=1.[Na]>C(O)C>[OH:20][C:19]1[C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:23]=[CH:24][C:7]([F:6])=[CH:8][CH:9]=2)=[C:15]([OH:16])[N:5]=[C:2]([CH3:3])[N:4]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 5360545SodiumHCID 66758678Dimethyl 2-(4-fluorobenzamido)malonate

Product 1

HCID 178433486HCID 178433486, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetamidine hydrochloride (1.05 g, 11.1 mmol) and dimethyl 2-(4-fluorobenzamido)malonate (1.0 g, 3.71 mmol) were added to a solution of sodium (0.26 g, 11.1 mmol) in ethanol (37 ml). The reaction mixture was refluxed for 3 hours. Then, after cooling, the solid product was collected and washed with ethanol. The product was dissolved in a minimal volume of water and acidified to pH 4-5 with 5M HCl. The precipitate was collected, washed with water and dried to give the title compound as a white solid (0.77 g, 79%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. temperatureThen, after cooling
  3. customthe solid product was collected
  4. washwashed with ethanol
  5. dissolutionThe product was dissolved in a minimal volume of water
  6. customThe precipitate was collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-01230a3df1af488da546e0816d8c55ec
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

Loading…