Methylamine → 5-(2-Methylaminoethoxy)benzofurazan hydrobromide

HRID 1195680Notes

Reaction equation

HRID 1195680 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9]([CH:13]=1)=[N:10][O:11][N:12]=2.[CH3:14][NH2:15]>C(O)C>[BrH:1].[CH3:14][NH:15][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9]([CH:13]=1)=[N:10][O:11][N:12]=2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 190453515-(2-Bromoethoxy)benzofurazan

Product 1

HCID 679164435-(2-Methylaminoethoxy)benzofurazan hydrobromideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(2-bromoethoxy)benzofurazan (0.84 g, 3.4 mmol) in ethanol (45 ml), contained within a Fisher-Porter pressure vessel cooled with ice/acetone was added methylamine (45 ml). The vessel was sealed, the bath removed and the solution was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue flushed with ethanol. Recrystallization from ethyl acetate-hexane gave 5-(2-methylaminoethoxy)benzofurazan hydrobromide (0.75 g, 81%); 1H NMR (DMSO) δ2.68 (s, 3H), 3.45 (t, 2H), 4.43 (t, 2H), 7.34 (m, 2H), 8.04 (d, 1H, J=9.6 Hz), 8.76 (bs, 2H).

Workup

  1. customThe vessel was sealed
  2. customthe bath removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue flushed with ethanol
  5. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7fb04d32d9d24b9cbaf05485b35f3a9d
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

Loading…