Bis(2-bromoethyl) ether → HCID 11617610, compound

HRID 1820157Notes

Reaction equation

HRID 1820157 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11](=[O:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C.Br[CH2:28][CH2:29][O:30][CH2:31][CH2:32]Br.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:8][C:6]1[CH:7]=[C:2]([N:1]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:3]([NH:10][C:11](=[O:17])[CH2:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[C:4]([CH3:9])[CH:5]=1

Participants

6

Reactant 4

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11609103HCID 11609103, compound

Product 1

HCID 11617610HCID 11617610, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

N-(2-Amino-4-bromo-6-methyl-phenyl)-3,3-dimethyl-butyramide (1v, 1.01 g), N,N-diisopropyl-ethylamine (1.80 mL) and bis(2-bromoethyl)ether (0.50 mL) were dissolved in dry N,N-dimethylformamide (5 mL) and heated to 180° C. for 50 minutes in a sealed microwave process vial. Saturated aqueous sodium bicarbonate (20 mL) was added and the mixture was extracted with ethyl acetate (3×20 mL), the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 0.740 g (60% yield) of the title compound as a white solid. LC-MS (m/z) 370 (MH+); tR=3.05, (UV, ELSD) 95%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.05 (s, 9H), 2.09 (s, 3H), 2.23 (s, 2H), 2.80 (t, 4H), 3.69 (t, 4H), 7.03 (d, 1H), 7.15 (d, 1H), 8.99 (s, 1H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-04011abf41ba4a8db596c28a9fb66984
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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