Acetic Anhydride → HCID 19608158, compound

HRID 1603108Notes

Reaction equation

HRID 1603108 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:32]=[CH:31][C:17]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)=[O:12].[OH-].[Na+].[C:39](OC(=O)C)(=[O:41])[CH3:40]>S(=O)(=O)(O)O>[C:39]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:32]=[CH:31][C:17]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)=[O:12])(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 19607839HCID 19607839, compound

Product 1

HCID 19608158HCID 19608158, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of 1-{4-[2-(6-aminohexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.70 g), acetic anhydride (20 ml) and two drops of conc. sulfuric acid is stirred at room temperature for 3 hours. To the reaction mixture is added aqueous 2N aqueous sodium hydroxide solution under ice-cooling and the mixture is extracted with chloroform. The organic layer is washed successively with water and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=200:1), and recrystallized from methanol/diethyl ether to give 1-{4-[2-(6-acetylaminohexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.60 g) as colorless needles, m.p. 171-172° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed successively with water and saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent is distilled off
  6. customthe resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=200:1)
  7. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-fd5b6756a8674f488d8bc71d4f4e9510
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

Loading…