Hydrogen Bromide → HCID 20450021, compound

HRID 358073Notes

Reaction equation

HRID 358073 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][CH:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[CH:23]=1.N([O-])=O.[Na+].C(=O)([O-])O.[Na+].[BrH:33]>CS(O)(=O)=O.O.[Cu]Br>[Br:33][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][CH:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[CH:23]=1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 20450007HCID 20450007, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20450021HCID 20450021, compound

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 962WaterSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 155 mg of 8-amino-6-(2-chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1]benzazepine in 1 ml of 2N methanesulphonic acid is cooled to 0° and treated with a solution of 44 mg of sodium nitrite in 0.2 ml of water. The mixture is stirred at 5° for 5 minutes and then added to a solution of 206 mg of copper (I) bromide in 2.4 ml of 48% hydrobromic acid. The mixture is stirred at room temperature for a further 10 minutes, whereupon it is neutralized with sodium hydrogen carbonate solution and extracted with chloroform. The chloroform extracts are dried and then evaporated. The residue is dissolved in chloroform and chromatographed on 5 g of silica gel. Impurities are eluted with chloroform and the desired product is eluted with chloroform/ethanol (19:1). After crystallization from ethyl acetate/ether, there is obtained 8-bromo-6-(2-chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1] benzazepine of melting point 250°-252°.

Workup

  1. stirringThe mixture is stirred at room temperature for a further 10 minutes, whereupon it
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform extracts are dried
  4. customevaporated
  5. dissolutionThe residue is dissolved in chloroform
  6. customchromatographed on 5 g of silica gel
  7. washImpurities are eluted with chloroform
  8. washthe desired product is eluted with chloroform/ethanol (19:1)
  9. customAfter crystallization from ethyl acetate/ether

Sources & evidence

ORD record
ord-0bf1b885b27f4740a8232a1d4adab03b
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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