Triethylamine → HCID 19874944, compound

HRID 465646Notes

Reaction equation

HRID 465646 reaction equation
[Br:1]CCC(Br)=O.[CH:7]([C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[C:11]=1[NH2:12])([CH3:9])[CH3:8].C(N([CH2:25][CH3:26])CC)C.C([O:30][CH2:31]C)(=O)C>>[CH3:18][CH:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:10]([CH:7]([CH3:9])[CH3:8])[C:11]=1[NH:12][C:31](=[O:30])[CH:25]([Br:1])[CH3:26])[CH3:19]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 32484DiisopropylanilineHCID 10998423Bromopropionylbromide

Product 1

HCID 19874944HCID 19874944, compoundYield 76.1%

Conditions

Temperature
25 °C

Procedure

Bromopropionylbromide (9.4 mL, 90 mmol) was added dropwise to a cooled (0° C.) solution of 2,6-diisopropylaniline (15.9 g, 89.7 mmol), and triethylamine (12.5 mL, 89.7 mmol) in ethyl acetate (1600 mL). The resulting slurry was warmed (25° C.) and stirred (1.5 hours, 25° C.). The resulting mixture was diluted with ethyl acetate (500 mL), washed with water (1×1000 mL), with 0.5N aqueous HCl (2×600 mL), with saturated aqueous sodium bicarbonate (1×600 mL), with brine (1×600 mL), then dried (MgSO4) and concentrated. The resulting solid was washed with cold ether and dried in a vacuum oven at 40° C. (16 hours) to yield 21.33 g (76.1%) of (±)-N-[2,6-bis(1-Methylethyl)phenyl]-2-bromopropanamide as a white solid.

Workup

  1. washwashed with water (1×1000 mL), with 0.5N aqueous HCl (2×600 mL), with saturated aqueous sodium bicarbonate (1×600 mL), with brine (1×600 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washThe resulting solid was washed with cold ether
  5. customdried in a vacuum oven at 40° C. (16 hours)

Sources & evidence

ORD record
ord-b11d5e66b384457bada332783408e51b
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

Loading…