Water → 10-Nitro-dibenz[b,f]azepin-5-carboxamide

HRID 637881Notes

Reaction equation

HRID 637881 reaction equation
S(=O)(=O)(O)O.[C:6]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([N+:19]([O-:21])=[O:20])=[CH:11][C:10]2[CH:22]=[CH:23][CH:24]=[CH:25][C:9]1=2)#[N:7].[OH2:26]>C(O)(=O)C.C(Cl)(Cl)Cl>[C:6]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([N+:19]([O-:21])=[O:20])=[CH:11][C:10]2[CH:22]=[CH:23][CH:24]=[CH:25][C:9]1=2)(=[O:26])[NH2:7]

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 2246789110-Nitro-5H-dibenz(b,f)azepine-5-carbonitrile

Product 1

HCID 59688910-Nitro-dibenz[b,f]azepin-5-carboxamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

2 ml of concentrated sulphuric acid are added dropwise to a suspension of 4.0 g (0.015 mole) of 5-cyano-10-nitro-5H-dibenz[b,f]azepine in 40 ml of acetic acid and the mixture is stirred for a further 15 hours at room temperature. 100 ml of water are gradually added to the clear solution, the precipitated material is taken up in chloroform, and the chloroform layer is washed with water and evaporated to dryness. After recrystallisation of the residue from isopropanol, pure 5-carbamoyl-10-nitro-5H-dibenz[b,f]azepine is obtained; melting point 208°-212°, yield 2.2 g, 52.4% of the theoretical yield. The analytical and spectroscopic data agree with the given structure.

Workup

  1. washthe chloroform layer is washed with water
  2. customevaporated to dryness
  3. customAfter recrystallisation of the residue from isopropanol

Sources & evidence

ORD record
ord-9b4cbc6fc220461489e2ac96b51033e8
Source dataset
uspto-grants-1985_12
Patent number
US04559174

Reaction notes

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