Ammonium Chloride → HCID 178519406, compound

HRID 478373Notes

Reaction equation

HRID 478373 reaction equation
[C:1]([CH2:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15](=[O:29])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][C:17]=2[Cl:28])[CH2:7][CH2:6][CH2:5]1)#[N:2].[Cl-].[NH4+].[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C)C=O>[NH:32]1[C:1]([CH2:3][CH:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]([C:15](=[O:29])[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][C:17]=3[Cl:28])[CH2:7][CH2:6][CH2:5]2)=[N:2][N:34]=[N:33]1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 18001036HCID 18001036, compound

Product 1

HCID 178519406HCID 178519406, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

5-Cyanomethyl-1-(4-phenyl-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (1 g), ammonium chloride (0.4 g) and sodium azide (0.48 g) are suspended in dimethylformamide (10 ml), and the mixture is heated at 110-120° C. for 16 hours. To the mixture are added ammonium chloride (0.4 g) and sodium azide (0.48 g), and the mixture is heated for 16 hours. The mixture is evaporated to remove dimethylformamide, and the resultant is acidified with a 1N hydrochloric acid. The mixture is extracted with chloroform, and the organic layer is washed with water, dried over magnesium sulfate, and concentrated. The residue is purified by silica gel column chromatography (solvent; dichloromethane→dichloromethane:methanol=20:1), and the resulting oily product is crystallized from diethyl ether to give 5-(5-tetrazolyl)methyl-1-(4-phenyl-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.9 g) as white powder.

Workup

  1. temperaturethe mixture is heated for 16 hours
  2. customThe mixture is evaporated
  3. customto remove dimethylformamide
  4. extractionThe mixture is extracted with chloroform
  5. washthe organic layer is washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane→dichloromethane:methanol=20:1)
  9. customthe resulting oily product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-672413e56fe84aeead12004cb08c00ff
Source dataset
uspto-grants-2003_11
Patent number
US06642223B2

Reaction notes

Loading…