Triethylamine → Triethylammonium bromide

HRID 536221

Reaction equation

HRID 536221 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:7]=1[NH2:8].[CH3:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19].N#C[Br:24]>C(Cl)Cl>[CH3:14][O:13][C:9]1[C:7]2[N:8]=[C:16]([NH2:17])[N:3]3[CH2:4][CH2:5][N:1]=[C:2]3[C:6]=2[CH:12]=[CH:11][CH:10]=1.[N:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:15].[BrH:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 583773572-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxyaniline

Product 2

HCID 2734074Triethylammonium bromideYield 296.1%HCID 178488375HCID 178488375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

2-(4,5-Dihydro-1H-imidazol-2-yl)-6-methoxyaniline (Step 3, 22.0 g, 115 mmol) and Et3N (48.1 mL, 345 mmol) were dissolved in CH2Cl2 (200 mL), cooled to 10° C. in an ice bath and cyanogen bromide (24.4 g, 230 mmol) was added portionwise. A slight exotherm was noted, and the reaction was stirred overnight. The reaction was concentrated under reduced pressure, then treated with EtOAc (150 mL) and concentrated under reduced pressure again. Finally, the residue was treated with Heptane and concentrated under reduced pressure to give the title compound as a mixture with Et3N.HBr (62 g, 99%): HPLC MS RT=1.08 min, MH+=217.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.85 (3H, s), 4.09-4.16 (2H, m), 4.31-4.38 (2H, m), 7.23 (1H, t), 7.31 (1H, d), 7.57 (1H, dd).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiontreated with EtOAc (150 mL)
  3. concentrationconcentrated under reduced pressure again
  4. additionFinally, the residue was treated with Heptane
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbf1799c49494e7eaaac2cf948a53bb4
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Linked notes

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