Sulfuric Acid → HCID 19607926, compound

HRID 1603111Notes

Reaction equation

HRID 1603111 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)=[O:5].[C:31](OC(=O)C)(=[O:33])[CH3:32].S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:29]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)=[O:5]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 19607946HCID 19607946, compound

Product 1

HCID 19607926HCID 19607926, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-[4-(2-chloro-4-aminobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.55 g), acetic anhydride (15 ml), acetic acid (5 ml) and a drop of sulfuric acid is stirred at room temperature for 1 hour. To the reaction mixture is added aqueous 2N aqueous sodium hydroxide solution and the mixture is extracted with chloroform. The extract is washed with saturated saline solution and dried over magnesium sulfate. The solvent is concentrated and the resulting residue is recrystallized from methanol/diethyl ether to give 1-[4-(2-chloro-4-acetylaminobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.28 g) as white powder, m.p. 214-243° C.

Workup

  1. extractionthe mixture is extracted with chloroform
  2. washThe extract is washed with saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent is concentrated
  5. customthe resulting residue is recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-dc46b2e4c2044613b2dd509f9b569a95
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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