Pyridine → HCID 2109630, compound

HRID 1754984Notes

Reaction equation

HRID 1754984 reaction equation
Cl[C:2]([CH2:4][O:5][C:6](=[O:8])[CH3:7])=[O:3].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[CH3:17].N1C=CC=CC=1>ClCCl>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:2]([CH2:4][O:5][C:6](=[O:8])[CH3:7])=[O:3])=[CH:12][C:11]=1[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 233594-Bromo-3-methylanilineHCID 26297Acetoxyacetyl chloride

Product 1

HCID 2109630HCID 2109630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Acetic acid chlorocarbonylmethyl ester (1.73 ml) was added to a solution of 4-bromo-3-methyl-phenylamine (2.0 g, 10.7 mmol) and pyridine (5.21 ml) in dichloromethane (20 ml), and the mixture was stirred at 40° C. for 2.5 hours. The mixture was cooled, and then quenched with water and extracted with dichloromethane. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure to give acetic acid (4-bromo-3-methyl-phenylcarbamoyl)-methyl ester (3.19 g).

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was sequentially washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c62fe7eb12af411882e5abda6848670f
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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