N-bromobutanimide → 8-Bromo-5,6-dimethyl-3-thia-1,4,7,8a-tetraaza-as-indacene

HRID 1051433Notes

Reaction equation

HRID 1051433 reaction equation
[CH3:1][C:2]1[C:13]2[N:9]([CH:10]=[N:11][C:12]=2[CH3:14])[C:8]2[N:7]=[CH:6][S:5][C:4]=2[N:3]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:10]1[N:9]2[C:13]([C:2]([CH3:1])=[N:3][C:4]3[S:5][CH:6]=[N:7][C:8]=32)=[C:12]([CH3:14])[N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 734258605,6-Dimethyl-3-thia-1,4,7,8a-tetraaza-as-indacene

Product 1

HCID 734258598-Bromo-5,6-dimethyl-3-thia-1,4,7,8a-tetraaza-as-indaceneYield 28.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

5,6-dimethyl-3-thia-1,4,7,8a-tetraaza-as-indacene (300 mg, 1.469 mmol) was dissolved in acetonitrile (50 ml) and 1-bromopyrrolidine-2,5-dione (131 mg, 0.734 mmol) was added. The resulting mixture was stirred at about 20° C. for about 1 h. After removal of the solvent under reduced pressure, the crude product was purified by prep-HPLC to give 60 mg of the title compound (yield: 15%).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-b08415d708b14386946a5df8eda3f605
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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