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

HRID 1733136Notes

Reaction equation

HRID 1733136 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-f346b66ca0f74710856de359163131a4
Source dataset
uspto-grants-1980_12
Patent number
USRE030456

Reaction notes

Loading…