Methane → Iminostilbene N-carbonylchloride

HRID 1439156Notes

Reaction equation

HRID 1439156 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.[C:16](Cl)([Cl:18])=[O:17].C>C1(C)C=CC=CC=1.C1C=CC=CC=1>[Cl:18][C:16]([N:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH:9]=[CH:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)=[O:17]

Participants

6

Reactant 3

HCID 297MethaneHCID 6371PhosgeneHCID 9212Dibenz(b,f)azepine

Product 1

HCID 182151Iminostilbene N-carbonylchloride

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1140TolueneSolvent

Procedure

To a slurry of 14.10g (0.073 mole) of dibenz[b,f]azepine in 60ml of dry toluene at room temperature was added dropwise a 120ml solution of 12.5% phosgene (excess) in benzene over 45 minutes. The resulting yellow slurry was stirred for 2 hours at room temperature, heated to reflux an additional 2 hours, and then stirred at room temperature overnight. Concentration of the reaction mixture by rotary evaporator in the hood gave a pale yellow solid which was taken up in 200ml benzene and treated with Norit-AR at boiling. The hot solution was filtered through celite, concentrated to one half of its original volume, cooled to room temperature and petroleum ether added to turbidity; white crystals of the named product precipitated. Yield, 14.4g, m.p. 145°-150°. Recrystallization from benzene-hexane afforded needles m.p. 150°-156.5°.

Workup

  1. temperatureheated
  2. temperatureto reflux an additional 2 hours
  3. stirringstirred at room temperature overnight
  4. customConcentration of the reaction mixture by rotary evaporator in the hood
  5. customgave a pale yellow solid which
  6. filtrationThe hot solution was filtered through celite
  7. concentrationconcentrated to one half of its original volume
  8. temperaturecooled to room temperature
  9. additionpetroleum ether added to turbidity
  10. customwhite crystals of the named product precipitated
  11. customYield
  12. customRecrystallization from benzene-hexane afforded needles m.p. 150°-156.5°

Sources & evidence

ORD record
ord-7e5051e944aa4e2484d43da2d6c0793a
Source dataset
uspto-grants-1977_11
Patent number
US04058511

Reaction notes

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