N-Bromoacetamide → s-Triazolo(5,1-a)isoquinoline, 2-phenyl-

HRID 616697Notes

Reaction equation

HRID 616697 reaction equation
[C:1]1([C:7]2[N:19]=[C:10]3[C:11]4[C:16]([CH2:17][CH2:18][N:9]3[N:8]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrNC(=O)C>C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2[N:19]=[C:10]3[C:11]4[C:16]([CH:17]=[CH:18][N:9]3[N:8]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4353N-BromoacetamideHCID 134397s-Triazolo(5,1-a)isoquinoline, 5,6-dihydro-2-phenyl-

Product 1

HCID 169678s-Triazolo(5,1-a)isoquinoline, 2-phenyl-Yield 79%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 0.5 g. (0.002 mole) of 2-phenyl-5,6-dihydro-s-triazolo[5,1-a]isoquinoline and 0.28 g. (0.002 mole) of N-bromoacetamide in 10 ml. of carbon tetrachloride is refluxed for 5 hours. The crystalline precipitate which forms is filtered and dissolved in methylene chloride. The resulting solution is washed with sodium bicarbonate, then the solvent is evaporated off and the obtained residue recrystallized from ethyl acetate. Yield 79%.

Workup

  1. additionA mixture of 0.5 g
  2. filtrationThe crystalline precipitate which forms is filtered
  3. dissolutiondissolved in methylene chloride
  4. washThe resulting solution is washed with sodium bicarbonate
  5. customthe solvent is evaporated off
  6. customthe obtained residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4ec79afd853a4edab48144e8f03942db
Source dataset
uspto-grants-1978_02
Patent number
US04075341

Reaction notes

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