Formamidine acetate → HCID 13271775, compound

HRID 464580Notes

Reaction equation

HRID 464580 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.C(O)(=O)C.[CH:58]([NH2:60])=[NH:59]>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:60][CH:58]=[N:59][CH:12]3[CH2:13][N:14]=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[CH:21]=1

Participants

8

Reactant 4

HCID 160693Formamidine acetateHCID 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 13271775HCID 13271775, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dropwise 9.5 mL (41 mmol) of a 4.3M methanol solution of sodium methoxide was added to a solution of 8.0 g (22.6 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 6.5 g (62.4 mmol) of formamidine acetate in 70 mL of ethanol. When the addition was complete stirring at room temperature was continued for 30 min. The reaction was diluted with water and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue was crystallized from a mixture of ether and petroleum ether to give a yellow solid. Recrystallization from a mixture of ether and methylene chloride gave pale yellow prisms, mp 150°-155°.

Workup

  1. additionWhen the addition
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was crystallized from a mixture of ether and petroleum ether
  7. customto give a yellow solid
  8. customRecrystallization
  9. additionfrom a mixture of ether and methylene chloride
  10. customgave pale yellow prisms, mp 150°-155°

Sources & evidence

ORD record
ord-140f7313b6ef42dc95034580338763a9
Source dataset
uspto-grants-1985_10
Patent number
US04548750

Reaction notes

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