Sulfuric Acid → HCID 131722635, compound

HRID 1067028Notes

Reaction equation

HRID 1067028 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[CH:5]1[CH:6]=[CH:7][C:8]2N[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:12]=[CH:11][C:9]=2[CH:10]=1.[S:20](=[O:24])(=[O:23])([OH:22])[OH:21]>C(O)(=O)C.O>[CH:5]1[CH:6]=[CH:7][C:8]2[N:1]([C:2]([NH2:4])=[O:3])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:9]=2[CH:10]=1.[S:20](=[O:22])(=[O:21])([OH:24])[OH:23]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 1176UreaHCID 9212Dibenz(b,f)azepine

Product 1

HCID 131722635HCID 131722635, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

To a suspension of urea (400 g, 6.66 mols) in acetic acid (500 ml), sulphuric acid (15 ml) was added, followed by iminostilbene (100 g, 0.518 mols), under stirring at 25-30° C. The resulting reaction mixture was heated to 80-85° C. and maintained for a period of 7-8 hours, and the reaction was monitored by thin layer chromatography (TLC). The reaction mass was diluted with water, and the resulting carbamazepine product (m.p. 188-189° C.) separated by filtration, washed with water until neutral and dried at 90-100° C. until constant weight. The identity of the product was further verified by tlc (toluene/methanol 18/03, uv=254 nm) to be identical to the reference compound and by infra-red spectroscopy (KBr) Vmax=3466, 1677, 1605, 1595 cm−1.

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. temperaturewas heated to 80-85° C.
  4. temperaturemaintained for a period of 7-8 hours
  5. customthe resulting carbamazepine product (m.p. 188-189° C.) separated by filtration
  6. washwashed with water until neutral and
  7. customdried at 90-100° C. until constant weight

Sources & evidence

ORD record
ord-c4458becaa394173bb07a6f08b6d3445
Source dataset
uspto-grants-2001_06
Patent number
US06245908B1

Reaction notes

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