Sodium Carbonate → HCID 9856409, compound

HRID 1934791Notes

Reaction equation

HRID 1934791 reaction equation
[C:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2].C([O-])([O-])=O.[Na+].[Na+].[Cl:24]Cl>C(Cl)Cl>[C:1]([N:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]([Cl:24])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24526ChlorineHCID 1116033810,11-Dihydro-5H-dibenzo[b,f]azepine-5-carbonitrile

Product 1

HCID 9856409HCID 9856409, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

50 ml of CH2Cl2 and 5 g (0.0227 mols) of (I) are loaded into a 250 ml pyrex round-bottom flask, under nitrogen and stirring, then 2.4 g of Na2CO3 (0.045 mols) are added thereto. The mixture is cooled to 0-5° C., irradiated from the outside with a 300 watt halogen lamp while adding a 1:1 chlorine and nitrogen gaseous mixture with 6 ml/minute flow, for 3 hours, then nitrogen for 10 minutes at the same flow rate. The mixture is filtered at 30° C. and methylene chloride is evaporated off. The residue is taken up with 15 ml of hexane and 4 ml of ethyl acetate, refluxed for 15 minutes, then cooled to 0° C. for 2 hours. The solid residue is recrystallized twice with the same solvent, to obtain 2.5 g (43% yield) of 5-cyano-10-chloro-10,11-dihydro-5H-dibenz[b,f]azepine (III) with melting point 139-140° C.

Workup

  1. waitnitrogen for 10 minutes at the same flow rate
  2. filtrationThe mixture is filtered at 30° C.
  3. custommethylene chloride is evaporated off
  4. temperaturerefluxed for 15 minutes
  5. temperaturecooled to 0° C. for 2 hours
  6. customThe solid residue is recrystallized twice with the same solvent

Sources & evidence

ORD record
ord-ee142f36cc674c0badbfa85f368598ab
Source dataset
uspto-grants-2002_05
Patent number
US06384217B1

Reaction notes

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