Triethylamine → 2-bromo-N-isopropyl-N-phenyl-acetamide

HRID 914693Notes

Reaction equation

HRID 914693 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl.Cl>[Br:18][CH2:19][C:20]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13032N-IsopropylanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 152160012-bromo-N-isopropyl-N-phenyl-acetamideYield 54.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-isopropylaniline (21.58 g, 180 mmol) in CH2Cl2 (350 mL) was added triethylamine (26.7 mL, 190 mmol). The solution was cooled to 0° C. and bromoacetyl bromide (14.0 mL, 160 mmol) was added slowly over 1 hour. The reaction was warmed to room temperature and was stirred for 24 hours. The reaction was diluted with 5% aqueous HCl. The organic solution was washed with 5% aqueous HCl (2×), aqueous NaHCO3 (1×), and brine (1×). The organic solution was filtered through a silica gel pad, eluting with CH2Cl2. Recrystallization from hexanes (60 mL) provided 22.47 g of 2-bromo-N-isopropyl-N-phenyl-acetamide. 1H NMR (CD2Cl2) δ 7.45 (m, 3H), 7.21 (m, 2H), 4.89 (m, 1H), 3.52 (s, 2H), 1.05 (d, 6H); MS 256.2 (M+1).

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. washThe organic solution was washed with 5% aqueous HCl (2×), aqueous NaHCO3 (1×), and brine (1×)
  3. filtrationThe organic solution was filtered through a silica gel pad
  4. washeluting with CH2Cl2
  5. customRecrystallization from hexanes (60 mL)

Sources & evidence

ORD record
ord-b86a8b05dbb343f785b107ec44b47cfa
Source dataset
uspto-grants-2007_09
Patent number
US07265104B2

Reaction notes

Loading…