Dibenz(b,f)azepine → Carbamazepine

HRID 1744396

Reaction equation

HRID 1744396 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[O-:16][C:17]#[N:18].[Na+]>C(O)(=O)C.C(O)C>[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:17]([NH2:18])=[O:16])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 9212Dibenz(b,f)azepineHCID 517096Sodium Cyanate

Product 1

HCID 2554CarbamazepineYield 80.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

30 g iminostilbene are heated to 60° C. in 360 ml acetic acid and 50 ml ethanol, and 20 g 98% sodium cyanate is added within 1.5 hours at this temperature. After a short heating to 80° C., the mixture is further stirred at 60° C., and then cooled to 15° C., sucked off, washed with 20 l acetic acid and dried to yield 29.4 g (80.3% of theoretical) of carbamazepine, having a melting point of 189° C. to 192° C.

Workup

  1. temperaturecooled to 15° C.
  2. washwashed with 20 l acetic acid
  3. customdried

Sources & evidence

ORD record
ord-25819033458c4515bfe6d3a3aa574b2d
Source dataset
uspto-grants-2006_03
Patent number
US07015322B1

Linked notes

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