Triethylamine → HCID 10731907, compound

HRID 343176Notes

Reaction equation

HRID 343176 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH:6]([N:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)C1C=CC=CC=1)([CH3:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[CH:6]([N:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[C:3](=[O:4])[CH2:2][Br:1])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 10966671HCID 10966671, compound

Product 1

HCID 10731907HCID 10731907, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromoacetyl bromide (8.76 mL) in methylene chloride (100 mL) is added dropwise to a 0° C. solution of N-Isopropyl-N-(3-methoxy-phenyl) aniline, prepared as in Part A, (16.22 g, 98.3 mmol) in methylene chloride (200 mL) and triethylamine (13.8 mL) and the resultant mixture is allowed to attain RT overnight. The reaction mixture is washed with 1N hydrochloric acid (3×100 mL), water (2×100 mL), brine (100 mL), dried (MgSO4), and concentrated in vacuo to afford N-Isopropyl-N-(3-methoxy-phenyl) bromoacetamide(23.16 g) as a dark mobile oil which is used without further purification: 1H NMR (300 MHz, CDCl3) δ7.38 (t, 1H, J=8.0), 7.01 (dd, 1H, J=8.1, 2.2), 6.81(d, 1H, J=7.6), 6.79 (s, 1H), 4.95 (m, 1H, J=6.8), 3.88 (s, 3H), 3.60 (s, 2H), 1.06 (d, 6H, J=6.8).

Workup

  1. washThe reaction mixture is washed with 1N hydrochloric acid (3×100 mL), water (2×100 mL), brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8477a3c39bf4d95b6674554f73190da
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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