Hydrochloric Acid → HCID 13285860, compound

HRID 543712Notes

Reaction equation

HRID 543712 reaction equation
[CH:1]1[C:11]2[C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.N1C=CC=CC=1.Cl>O1CCOCC1>[N:22]1[CH:23]=[CH:24][C:19]([C:18]([N:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]2=3)=[O:25])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 2013275,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-oneHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 13285860HCID 13285860, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 21.0 g (0.1 mol) of 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one, 23.0 g (0.129 mol) of isonicotinic acid chloride hydrochloride, 21 ml (0.26 mol) of pyridine and 300 ml of anhydrous dioxan was refluxed for 3 hours. After cooling, the mixture was poured into 1 liter of ice-cold water, acidified with conc. hydrochloric acid and extracted twice, each time with 200 ml of dichloromethane. The aqueous phase was made alkaline with methylene chloride. The combined methylene chloride extracts were washed with water, dried over sodium sulphate and the solvent was removed in vacuo. The residue was recrystallized from hot methanol. After washing with ether, the beige crystals melted at 277°-279° C. Yield 16.0 g (51% of theory).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted twice
  4. washThe combined methylene chloride extracts were washed with water
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was removed in vacuo
  7. customThe residue was recrystallized from hot methanol
  8. washAfter washing with ether

Sources & evidence

ORD record
ord-32222269a7d647b39742941f683db6ab
Source dataset
uspto-grants-1984_05
Patent number
US04447434

Reaction notes

Loading…