Acetamidine monohydrochloride → HCID 13225498, compound

HRID 1979553Notes

Reaction equation

HRID 1979553 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6](=O)[C:7](=[CH:17]N(C)C)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.Cl.[C:25]([NH2:28])(=[NH:27])[CH3:26].C[O-].[Na+]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[N:28]=[C:25]([CH3:26])[N:27]=[CH:17][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 67170Acetamidine monohydrochloride3×HCID 10942334Sodium Methoxide3×HCID 53830000HCID 53830000, compound

Product 1

HCID 13225498HCID 13225498, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1.6 g (0.005 mol) of 8-chloro-3,4-dihydro-4-(dimethylaminomethylene)-1-phenyl-5H-2-benzazepin-5-one and 0.7 g (0.0075 mol) of acetamidine hydrochloride in 50 ml of methanol was stirred at room temperature, under argon, and treated with 0.8 g (0.015 mol) of sodium methylate in one portion. After stirring for 10 min, 30 ml of methylene chloride was added and stirring was continued. Another 0.8 g (0.015 mol) of sodium methylate and 0.7 g (0.0075 mol) of acetamidine hydrochloride were added after 2 hrs. The addition of 0.015 mol of sodium methylate and 0.0075 mol of acetamidine hydrochloride was repeated after another 2 hr and stirring at room temperature was continued overnight. After diluting with 50 ml of methylene chloride, the mixture was washed with water, dried over sodium sulfate and evaporated at reduced pressure. Crystallization occurred when the residue was dissolved in 20 ml of warm hexane and cooled. Evaporation of the solvent gave a second crop of product. Recrystallization from hexane (charcoal) gave off-white crystals: mp 120°-122° C.

Workup

  1. stirringAfter stirring for 10 min
  2. stirringstirring
  3. stirringstirring at room temperature
  4. waitwas continued overnight
  5. washthe mixture was washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated at reduced pressure
  8. customCrystallization
  9. dissolutionwas dissolved in 20 ml of warm hexane
  10. temperaturecooled
  11. customEvaporation of the solvent
  12. customgave a second crop of product
  13. customRecrystallization from hexane (charcoal)
  14. customgave off-white crystals

Sources & evidence

ORD record
ord-2ff9946c03574459bf99632a454de0a5
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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