Chloroform → HCID 12412205, compound

HRID 1730260Notes

Reaction equation

HRID 1730260 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-:16].[CH2:17]([N+](C1C=CC=CC=1)(C)C)C1C=CC=CC=1.[CH:33]([Cl:36])(Cl)Cl.[OH-:37].[Na+]>O>[Cl:16][C:33]1([Cl:36])[CH:9]2[CH:10]1[C:11]1[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=1[N:6]([CH:17]=[O:37])[C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=12

Participants

6

Reactant 4

HCID 6212ChloroformHCID 9212Dibenz(b,f)azepineHCID 14798Sodium Hydroxide2×HCID 76668Phenyldimethylbenzylammonium chloride

Product 1

HCID 12412205HCID 12412205, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

At 40° C, 14.48 g. (0.075 mole) of 5H-dibenz(b,f)azepine, 0.57 g. (0.0023 mole) of benzylphenyldimethylammonium chloride, 538 g. (4.5 moles)of chloroform and 360 g. of a 33 % aqueous solution of sodium hydroxide (3.0 moles) are stirred together for 6 hours, after which time 216 g. (5.4moles) of solid sodium hydroxide and 60 g. of water are added. The mixture is stirred at 40° C for 16 hours and the resulting solution is extracted with chloroform. The chloroform extract is washed with water anddried with anhydrous sodium sulfate, followed by distillation of the solvent to dry up under reduced pressure. The residue is then recrystallized from benzene to give 1,1-dichloro-1a,10b-dihydrodibenzo(b,f)cycloprop(d)azepine-6(1H)-carboxaldehyde in a yield of 77.5 % (17.67 g.). Melting point 213° C(decomp.)

Workup

  1. customAt 40° C
  2. extractionthe resulting solution is extracted with chloroform
  3. extractionThe chloroform extract
  4. washis washed with water
  5. distillationfollowed by distillation of the solvent
  6. customto dry up under reduced pressure
  7. customThe residue is then recrystallized from benzene

Sources & evidence

ORD record
ord-b630db64efbc450984e8e6e3489dd3cf
Source dataset
uspto-grants-1976_11
Patent number
US03992370

Reaction notes

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