Ammonia → 2-Benzothiazolemethanamine, 5-bromo-

HRID 525533Notes

Reaction equation

HRID 525533 reaction equation
[NH3:1].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11]Br)=[N:8][C:7]=2[CH:13]=1>CO>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11][NH2:1])=[N:8][C:7]=2[CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 144586425-Bromo-2-(bromomethyl)-1,3-benzothiazole

Product 1

HCID 433062172-Benzothiazolemethanamine, 5-bromo-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Gaseous ammonia is bubbled through a solution of 5-Bromo-2-bromomethyl-benzothiazole (0.850 g, 2.768 mmol) in methanol (16 mL) for 10 minutes at 0° C. then stirred at room temperature for 3 hours. The reaction mixture is dried over magnesium sulfate, filtered and the solvent is evaporated in vacuo. The crude material is washed with n-pentane and hexane to afford the title compound (0.78 g). 1H NMR (400 MHz, DMSO-d6) δ: 4.52 (s, 2H), 7.69-7.72 (dd, J1=1.96 Hz, J2=8.68 Hz, 1H), 7.95 (d, J=8.64 Hz, 1H), 8.46 (d, J=1.96 Hz, 1H). LC-MS (m/z): [M+H]=245.0.

Workup

  1. dry with materialThe reaction mixture is dried over magnesium sulfate
  2. filtrationfiltered
  3. customthe solvent is evaporated in vacuo
  4. washThe crude material is washed with n-pentane and hexane

Sources & evidence

ORD record
ord-c9c186ad86ca4fbdb186dadb0af4623d
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

Loading…