Triethylamine → HCID 10755599, compound

HRID 343171Notes

Reaction equation

HRID 343171 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH:6]([N:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])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]=[CH:18][C:17]=1[O:22][CH3:23])[C:3](=[O:4])[CH2:2][Br:1])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromide2×HCID 54250348HCID 54250348, compound

Product 1

HCID 10755599HCID 10755599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromoacetyl bromide (7.8 mL) in methylene chloride (125 mL) is added dropwise to a 0° C. solution of N-Isopropyl-N-(2-methoxy-phenyl) aniline, prepared as in Part A, (14.51 g, 87.9 mmol) in methylene chloride (125 mL) and triethylamine (12.3 mL) and the resultant mixture is allowed to attain RT overnight. After 18 h an additional 2.0 mL of bromoacetyl bromide is added and the resultant reaction mixture stirred at RT for 4 h. 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-(2-methoxy-phenyl) bromoacetamide(20.3 g) as a dark mobile oil which is used without further purification: 1H NMR (300 MHz, CDCl3) δ7.45 (dt, 1H, J=7.8, 1.4), 7.20 (dd, 1H, J=7.8, 1.4), 7.04 (m, 2H), 4.90 (m, 1H, J=6.8), 3.85 (s, 3H), 3.60 (dd, 2H, J=32.9, 11.5), 1.20 (d, 3H, J=6.8), 0.97 (d, 3H, J=6.8).

Workup

  1. customthe resultant reaction mixture
  2. washThe reaction mixture is washed with 1N hydrochloric acid (3×100 mL), water (2×100 mL), brine (100 mL)
  3. customdried
  4. concentration(MgSO4) and concentrated in vacuo

Sources & evidence

ORD record
ord-cca5d7f34d4149e69066355ab3c855d3
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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