Bromine → HCID 135730604, compound

HRID 354193Notes

Reaction equation

HRID 354193 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:20])[C:13]3[C:14](=[CH:16][N:17]([CH3:19])[N:18]=3)[N:15]=2)=[CH:8][C:7]([N+:21]([O-:23])=[O:22])=[CH:6][N:5]=1)[CH3:2].[Br:24]Br.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:24][C:16]1[N:17]([CH3:19])[N:18]=[C:13]2[C:12](=[O:20])[NH:11][C:10]([C:9]3[C:4]([O:3][CH2:1][CH3:2])=[N:5][CH:6]=[C:7]([N+:21]([O-:23])=[O:22])[CH:8]=3)=[N:15][C:14]=12

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 517045Sodium AcetateHCID 135730625HCID 135730625, compound

Product 1

HCID 135730604HCID 135730604, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the title compound of Example 52 (6.9 g, 21.8 mmol), bromine (1.35 mL, 26.2 mmol), and sodium acetate (2.7 g, 32.7 mmol) in acetic acid (100 mL) was heated under reflux for 7 h, then allowed to cool. Additional bromine (0.35 mL, 6.8 mmol) was added and the reaction stirred at room temperature for a further 18 h. The reaction mixture was concentrated under reduced pressure and azeotroped with toluene. The residue was partitioned between dichloromethane and water and the resulting precipitate filtered off, washed with dichloromethane, water, then diethyl ether and dried.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 h
  3. temperatureto cool
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customazeotroped with toluene
  6. customThe residue was partitioned between dichloromethane and water
  7. filtrationthe resulting precipitate filtered off
  8. washwashed with dichloromethane, water
  9. dry with materialdiethyl ether and dried

Sources & evidence

ORD record
ord-bae9c5d546fe4449b6c8ab03ff3c5c12
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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