Hexane → HCID 13225509, compound

HRID 464526Notes

Reaction equation

HRID 464526 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=O)[C:7](=[CH:18][N:19](C)[CH3:20])[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.C(O)(=O)C.C(N)=[NH:30].C[O-].[Na+].CCCCCC>CO>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:30]=[CH:20][N:19]=[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 4

HCID 8058HexaneHCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 54487933HCID 54487933, compound

Product 1

HCID 13225509HCID 13225509, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 34.2 g (0.1 mole) of 8-chloro-3,4-dihydro-1-(2-fluorophenyl)-4-[(dimethylamino)methylene]-5H-2-benzazepin-5-one, 62.4 g (0.6 mole) of formamidine acetate, and 35 g (0.63 mole) of sodium methoxide in 700 ml of methanol was stirred at room temperature for 3 hr, while bubbling nitrogen through the solution. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a red oil. The oil was suspended in boiling hexane and the hexane solution decanted. Upon cooling the end product was collected by filtration. Recrystallization from cyclohexane gave off-white crystals, mp 123°-125° C.

Workup

  1. customwhile bubbling nitrogen through the solution
  2. additionThe mixture was diluted with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto give a red oil
  7. customthe hexane solution decanted
  8. temperatureUpon cooling the end product
  9. filtrationwas collected by filtration
  10. customRecrystallization from cyclohexane
  11. customgave off-white crystals, mp 123°-125° C.

Sources & evidence

ORD record
ord-c9e7f35674e742cb8000a43512aea425
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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