ChemicalBook CAS DataBase List Carbamazepine

Carbamazepine synthesis

9synthesis methods

Product Name:Carbamazepine
CAS Number:298-46-4
Molecular formula:C15H12N2O
Molecular Weight:236.27

Carbamazepine, 5H-dibenz[b,f]azepine-5-carboxamide (9.5.2), is synthesized by reacting 5H-dibenz[b,f]azepine and phosgene, which forms 5-chlorcarboxy- 5H-dibenz-[b,f]azepine (9.5.1), and its subsequent reaction with ammonia to give the desired carbamazepine (9.5.2) [16]. An alternative method of synthesis is the direct reaction of 5H-dibenz[b,f]azepine with potassium cyanate [17].

256-96-2
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917-61-3 Synthesis

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298-46-4
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$7.00/1g

Yield:298-46-4 98.8%

Reaction Conditions:

in water;acetic acid at 15 - 60; for 4 h;Product distribution / selectivity;

Steps:

6

3 kg iminostilbene are stirred in a mixture of 28.5 l acetic acid and 1.5 l water, and heated to 60° C. Within about 2 hours 1.66 kg 98% sodium cyanate is added, the the mixture is cooled to 15° C. and held for a further 2 hours between 15° C. to 20° C., then the crystals are sucked off, washed with 2 l acetic acid and dried, yielding 3.39 kg (92.5% of theoretical) of the end product, having a melting point of 190° C. to 192° C.Next 22 l acetic acid was distilled off, 10 l water was added to the residue, briefly stirred, sucked off and washed with 5 l water and dried and a further 0.28 kg of the product was obtained which was recrystallized from toluene to 0.23 kg (6.3% of theoretical) having a melting point of 191° C. to 194° C. This resulted in a total yield of 98.8% of theoretical).

References:

US7015322,2006,B1 Location in patent:Page/Page column 4