Benzamidine, hydrochloride → HCID 135453348, compound

HRID 962856Notes

Reaction equation

HRID 962856 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[O-:12].[Na+].[CH3:14][O:15][C:16]1[CH:34]=[CH:33][C:19]2[C:20](=O)[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)O[C:18]=2[CH:17]=1>CO.C(Cl)(Cl)Cl>[OH:12][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]1[N:10]=[C:20]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:34][CH:33]=2)[N:21]=[C:22]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[N:9]=1

Participants

6

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 10942334Sodium MethoxideHCID 19086186HCID 19086186, compound

Product 1

HCID 135453348HCID 135453348, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

4.9 g (10.86 mmol) of benzamidine hydrochloride (38% in methanol) and then a solution of 1.95 g (10.86 mmol) of sodium methoxide (30% in methanol) are added to a suspension of 2.83 g (10 mmol) of 7-methoxy-2-(4-methoxyphenyl)-4H-1,3-benzoxazin-4-one in 48 ml of methanol. The mixture is heated to boiling and diluted with 38 ml of methanol. After refluxing (30 minutes), the precipitate is filtered off with suction while hot and washed twice with 10 ml of methanol each time. Recrystallization from chloroform/petroleum ether gives 3.74 g (97% of theory) of the product of the formula ##STR25## M.p.: 171°-172° C. UV spectrum (2.25·10-5 mol in chloroform) λmax /εmax =297/34920 325/shoulder

Workup

  1. temperatureThe mixture is heated
  2. temperatureAfter refluxing (30 minutes)
  3. filtrationthe precipitate is filtered off with suction while hot and
  4. washwashed twice with 10 ml of methanol each time
  5. customRecrystallization from chloroform/petroleum ether
  6. customgives 3.74 g (97% of theory) of the product of the formula ##STR25## M.p.: 171°-172° C

Sources & evidence

ORD record
ord-125b258225764cdab857a16a16d6910b
Source dataset
uspto-grants-1998_06
Patent number
US05760111

Reaction notes

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