Hydrochloric Acid → HCID 18917354, compound

HRID 54757Notes

Reaction equation

HRID 54757 reaction equation
[Cl-].[NH4+].[N-:3]=[N+:4]=[N-:5].[Na+].[C:7]([CH2:9][CH:10]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[N:14]([C:22](=[O:40])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])=[CH:25][C:24]=2[CH3:39])[CH2:13][CH2:12][CH2:11]1)#[N:8].Cl.[CH3:42]N(C)C=O>>[CH3:42][N:3]1[C:7]([CH2:9][CH:10]2[C:16]3[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22](=[O:40])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[Cl:37])=[CH:25][C:24]=3[CH3:39])[CH2:13][CH2:12][CH2:11]2)=[N:8][N:5]=[N:4]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 199583775-cyanomethyl-7-chloro-1-[2-methyl-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Product 1

HCID 18917354HCID 18917354, compound

Conditions

Temperature
100 °C

Procedure

0.14 g of ammonium chloride and 0.17 g of sodium azide were added to a solution of 0.7 g of 5-cyanomethyl-7-chloro-1-[2-methyl-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine dissolved in 10 ml of dry dimethylformamide. The mixture was stirred at 100° C. for 2 hours. To the reaction mixture was added hydrochloric acid to control the pH of the mixture at about 2, followed by extraction with ethyl acetate. The organic layer was water-washed, then dried and subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol =30/1) to obtain 0.52 g of 5-(1-methyl-1,2,3,4-tetrazol-5-yl)methyl-7-chloro-1-[2-methyl-4-(2-chlorobenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashed
  3. customdried
  4. distillationsubjected to vacuum distillation
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol =30/1)

Sources & evidence

ORD record
ord-3b74f54adde3455a9f3c1a2b1c4a4e11
Source dataset
uspto-grants-1997_04
Patent number
US05622947

Reaction notes

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