Bromine → 9-Bromo-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine

HRID 963052Notes

Reaction equation

HRID 963052 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[CH:20]=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[Br:23]Br>ClC(Cl)C>[Br:23][C:20]1[N:12]2[C:13]3[S:17][C:16]([CH2:18][CH3:19])=[CH:15][C:14]=3[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:9][CH2:10][C:11]2=[N:22][N:21]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 124343254-(2-chlorophenyl)-2-ethyl-6H-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine

Product 1

HCID 677276859-Bromo-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-(2-Chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (10 g) was dissolved in dichloroethane (100 ml), and bromine (1.7 ml) was added under ice-cooling. The mixture was heated to room temperature, and allowed to stand overnight. The solvent was evaporated, and chloroform was added. The mixture was washed with an aqueous sodium thiosulfate solution, a saturated aqueous sodium hydrogencarbonate solution and brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-hexane) and crystallized from ethyl acetate to give 3.4 g of 9-bromo-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. additionchloroform was added
  4. washThe mixture was washed with an aqueous sodium thiosulfate solution
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution and brine, and dried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-hexane)
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-39a8547a74554fbab2625d412e5c03c9
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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