Acetamidine monohydrochloride → HCID 13271777, compound

HRID 464578Notes

Reaction equation

HRID 464578 reaction equation
C[O-].[Na+].C([O:8][C:9]([CH:11]1[C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:14][CH:13]=[CH:12]1)=O)CCC.C(OC(C1C2C=CC(Cl)=CC=2C(C2C=CC=CC=2)=NCC=1)=O)CCC.Cl.[C:55]([NH2:58])(=[NH:57])[CH3:56]>C(O)C.O.CO>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]2[CH:11]3[C:9](=[O:8])[NH:58][C:55]([CH3:56])=[N:57][CH:12]3[CH2:13][N:14]=[C:15]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:16]=2[CH:21]=1

Participants

8

Reactant 4

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 13271771Butyl 8-chloro-1-phenyl-3H-2-benzazepine-5-carboxylateHCID 13271773Butyl 8-chloro-1-phenyl-5H-2-benzazepine-5-carboxylate

Product 1

HCID 13271777HCID 13271777, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In one portion, 11.5 mL (49 mmol) of a 4.34M methanol solution of sodium methoxide was added to a solution of 11.0 g (31 mmol) of a mixture of 8-chloro-1-phenyl-5H-2-benzazepine-5-carboxylic acid butyl ester and 8-chloro-1-phenyl-3H-2-benzazepine-5-carboxylic acid butyl ester and 5.7 g (60 mmol) of acetamidine hydrochloride in 200 mL of ethanol. The mixture was refluxed for 18 hr, cooled and poured into 800 mL of water. The resulting precipitate was collected by filtration and washed with ether to yield a yellow solid. Recrystallization from tetrahydrofuran gave off-white prisms, mp 155°-160°.

Workup

  1. temperatureThe mixture was refluxed for 18 hr
  2. temperaturecooled
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with ether
  5. customto yield a yellow solid
  6. customRecrystallization from tetrahydrofuran
  7. customgave off-white prisms, mp 155°-160°

Sources & evidence

ORD record
ord-76f4b5bdb3b647938af315da0b80d509
Source dataset
uspto-grants-1985_10
Patent number
US04548750

Reaction notes

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