2,2-Diethoxyethylamine → HCID 178467945, compound

HRID 471823Notes

Reaction equation

HRID 471823 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([C:9](=[NH:12])OC)[CH:6]=[CH:7][CH:8]=1.[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH2:18])[CH3:14]>CO>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH:18][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Br:2])[CH:4]=1)=[NH:12])[CH3:14]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 14685566Methyl 3-bromobenzimidate hydrochloride

Product 1

HCID 178467945HCID 178467945, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-bromobenzenecarboximidoate hydrochloride (Step 1 above) in MeOH (10 mL) at 0° C. was added [2,2-bis(ethyloxy)ethyl]amine (1.74 mL; 12 mmol) in one portion and the mixture was gradually warmed to room temperature (overnight). The mixture was concentrated in vacuo, partitioned between CH2Cl2/1M NaOH and the layers were separated. The aqueous layer was extracted with CH2Cl2 (×2), combined organics were washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo affording the title compound as a light brown oil which was used directly for Step 3 below. LC/MS (method A) tR 1.25 min, m/z 315, 317 (M+H, Br isotopes, 4%), 223, 225 (M+H−2EtOH, Br isotopes, 100%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between CH2Cl2/1M NaOH
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (×2)
  5. washcombined organics were washed (H2O, brine)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-838497316b9c4e5ead04a5837b5021eb
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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