Water → HCID 20229732, compound

HRID 2291150Notes

Reaction equation

HRID 2291150 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].O.[Br:11]Br>C(O)(=O)CC>[BrH:11].[Br:11][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:2]([CH3:1])[C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 962WaterHCID 72502,4-DimethylanilineHCID 24408Bromine

Product 1

HCID 20229732HCID 20229732, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent2×

Procedure

A 1 1, 3-necked round-bottom flask, equipped with an overhead stirrer, thermometer, and addition funnel was placed in a heating mantle and charged with 2,4-dimethylaniline (60 g, 0.495 mol), propionic acid (450 ml) and water (2 ml). Rapid stirring was initiated as a solution of bromine (93 g, 0.582 mol) in propionic acid (50 ml) was added over 5 minutes. The resulting slurry was stirred at 85°-90° C. for 40 minutes while monitoring the progress of the reaction by high pressure liquid chromatography (HPLC). After cooling to ambient temperature, ethylene was bubbled through the mixture to discharge the color. After cooling to 10° C. and a 15 minute age, the mixture was filtered. The product was washed with chilled propionic acid (150 ml) then hexane (400 ml) added portionwise. The white to cream colored solid was air dried with final drying accomplished under vacuum. The Compound 1a was obtained as a fine white powder.

Workup

  1. customA 1 1, 3-necked round-bottom flask, equipped with an overhead stirrer
  2. additionthermometer, and addition funnel
  3. additionwas added over 5 minutes
  4. stirringThe resulting slurry was stirred at 85°-90° C. for 40 minutes
  5. customthe progress of the reaction by high pressure liquid chromatography (HPLC)
  6. customethylene was bubbled through the mixture
  7. temperatureAfter cooling to 10° C. and a 15 minute age
  8. filtrationthe mixture was filtered
  9. washThe product was washed with chilled propionic acid (150 ml)
  10. additionhexane (400 ml) added portionwise
  11. customdried
  12. customwith final drying

Sources & evidence

ORD record
ord-25882a114e3e4d69b34676f1e957b57a
Source dataset
uspto-grants-1986_10
Patent number
US04620025

Reaction notes

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