Bromine → HCID 20450024, compound

HRID 358071Notes

Reaction equation

HRID 358071 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12](=[O:15])[NH:13][N:14]=[C:10]3[CH2:9][CH2:8][CH:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1.BrBr>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12](=[O:15])[NH: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[F:22])[C:6]=2[CH:23]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 20449987HCID 20449987, compound

Product 1

HCID 20450024HCID 20450024, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 660 mg of 8-chloro-6-(2-fluorophenyl)-2,4,5,6-tetrahydro-1H-s-triazolo[4,3-a][1]benzazepin-1-one in 150 ml of carbon tetrachloride is treated with 0.11 ml of bromine and heated to boiling while stirring for 2 hours while irradiating with a 500 W incandescent lamp. The solution is evaporated in vacuo. The residue is dissolved in chloroform and the solution is washed twice with saturated sodium hydrogen carbonate solution, dried and evaporated in vacuo. The residue is chromatographed on 35 g of silica gel. By elution with toluene/ethyl acetate (4:1) and crystallization from ethyl acetate/ether there is obtained 8-chloro-6-(2-fluorophenyl)-2,4-dihydro-1H-s-triazolo[4,3-a][1]benzazepin-1-one of melting point 221°-224°.

Workup

  1. temperatureheated
  2. customwhile irradiating with a 500 W incandescent lamp
  3. customThe solution is evaporated in vacuo
  4. dissolutionThe residue is dissolved in chloroform
  5. washthe solution is washed twice with saturated sodium hydrogen carbonate solution
  6. customdried
  7. customevaporated in vacuo
  8. customThe residue is chromatographed on 35 g of silica gel
  9. washBy elution
  10. customwith toluene/ethyl acetate (4:1) and crystallization from ethyl acetate/ether there

Sources & evidence

ORD record
ord-5737726de2d348dc8825c65b16dd33cf
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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