2,6-Dimethylaniline → HCID 2781531, compound

HRID 2217168Notes

Reaction equation

HRID 2217168 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)(O)[O-].[Na+].[Br:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>CCOCC>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:18](=[O:19])[CH2:17][CH2:16][Br:15]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 84944Propanoyl chloride, 3-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 2781531HCID 2781531, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 2,6-dimethylaniline (2 g, 16.5 mmol), diethyl ether, and aqueous saturated sodium bicarbonate (50:50 v/v) was added dropwise 3-bromopropionoyl chloride (2 g, 19.8 mm) in ether (5 mL). The mixture was allowed to stir at 0° C. for 2 hours, and at room temperature for an additional 1 hour. The organic layer was washed with 10% citric acid, dried over MgSO4, then filtered. The solvent was evaporated to afford N-(2,6-dimethylphenyl)-3-bromopropanamide, a compound of formula (1), as a white solid.

Workup

  1. waitat room temperature for an additional 1 hour
  2. washThe organic layer was washed with 10% citric acid
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-dae1cce638ef4d498ced7bbad09384ef
Source dataset
uspto-grants-2008_08
Patent number
US07407960B2

Reaction notes

Loading…