Acetamidine monohydrochloride → HCID 13225499, compound

HRID 464158Notes

Reaction equation

HRID 464158 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=O)[C:7](=[CH:18]N(C)C)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1.Cl.[C:26]([NH2:29])(=[NH:28])[CH3:27].C[O-].[Na+]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:29]=[C:26]([CH3:27])[N:28]=[CH:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 67170Acetamidine monohydrochloride3×HCID 10942334Sodium Methoxide3×HCID 54487933HCID 54487933, compound

Product 1

HCID 13225499HCID 13225499, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 5.1 g (0.015 mol) of 8-chloro-1-(2-fluorophenyl)-3,4-dihydro-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one and 2.1 g (0.0225 mol) of acetamidine hydrochloride in 150 ml of methanol was stirred at room temperature under argon, and treated with 2.4 g (0.045 mol) of sodium methylate in one portion. After stirring for 10 min, 90 ml of methylene chloride was added and stirring was continued. Another 2.4 g (0.045 mol) of sodium methylate and 2.1 g (0.0225 mol) of acetamidine hydrochloride were added after 2 hrs. The addition of 0.045 mol of sodium methylate and 0.0225 mol of acetamidine hydrochloride was repeated after another 2 hr interval and stirring at room temperature was continued overnight. After diluting with 150 ml of methylene chloride, the mixture was washed with water, dried over sodium sulfate and evaporated at reduced pressure. Recrystallization of the residue from hexane (charcoal) gave white crystals: mp 104°- 107° C.

Workup

  1. stirringAfter stirring for 10 min
  2. stirringstirring
  3. stirringinterval and stirring 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. customRecrystallization of the residue from hexane (charcoal)
  9. customgave white crystals

Sources & evidence

ORD record
ord-014427956239457d9e49de9ee228ebdb
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

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