ar-Bromo-ar-nitrobenzenamine → HCID 131734569, compound

HRID 595147

Reaction equation

HRID 595147 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1)[NH2:5].Cl[C:13]1[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:13]2[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1

Participants

4

Reactant 2

HCID 44535ar-Bromo-ar-nitrobenzenamineHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidine

Product 1

HCID 131734569HCID 131734569, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

was added to a solution of 3-bromo-5-nitroaniline (3.4 g, 15.7 mmol) and 2-chloro-4-(trifluoromethyl)pyrimidine) (2.27 mL, 18.80 mmol) in dioxane (78 ml) at room temperature, under nitrogen. The mixture became heterogeneous instantly and upon heating, a solution was obtained. The mixture was stirred at 100° C. for 18 hours then cooled to room temperature and concentrated under reduced pressure. Saturated sodium bicarbonate and dichloromethane were added, the organic phase was recovered using a phase separator and then concentrated under reduced pressure. The residue was washed in hexanes/ether and filtered to afford N-(3-bromo-5-nitrophenyl)-4-(trifluoromethyl)pyrimidin-2-amine.

Workup

  1. temperatureupon heating
  2. customa solution was obtained
  3. temperaturethen cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionSaturated sodium bicarbonate and dichloromethane were added
  6. customthe organic phase was recovered
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed in hexanes/ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-6ad4c9f2656f41ba9b88245c8b6389b4
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Linked notes

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