Ammonia → HCID 19607870, compound

HRID 1603110Notes

Reaction equation

HRID 1603110 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:35]=[CH:34][CH:33]=[CH:32][C:9]=1[C:10]([NH:12][C:13]1[CH:31]=[CH:30][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:15][CH:14]=1)=[O:11])=O)C.[NH3:36].[Cl-].[NH4+]>CO>[C:4]([CH2:6][O:7][C:8]1[CH:35]=[CH:34][CH:33]=[CH:32][C:9]=1[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:30][CH:31]=1)=[O:11])(=[O:3])[NH2:36]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 19607790HCID 19607790, compound

Product 1

HCID 19607870HCID 19607870, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[4-(2-ethoxycarbonylmethoxybenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.00 g), aqueous ammonia (100 ml), ammonium chloride (0.3 g) and methanol (150 ml) is heated at 100° C. for 4 hours in a sealed tube. The solvent is distilled off and the resulting residue is extracted with chloroform, washed successively with water and saturated saline solution, and dried over magnesium sulfate. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=50:1), and recrystallized from methanol/diethyl ether to give 1-[4-(2-carbamoylmethoxybenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.43 g) as white powder, m.p. 198-199° C.

Workup

  1. distillationThe solvent is distilled off
  2. extractionthe resulting residue is extracted with chloroform
  3. washwashed successively with water and saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solvent is concentrated
  6. customthe resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=50:1)
  7. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-aaffdbd7133145759621e7a4a904dc95
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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