Sodium Iodide → 5-({3-[(4-Methoxybenzyl)amino]propyl}amino)-2-methyl-1,3-benzothiazole-4,7-dione

HRID 908672Notes

Reaction equation

HRID 908672 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+].Br[CH2:23][CH2:24][CH2:25][NH:26][C:27]1[C:36](=[O:37])[C:31]2[N:32]=[C:33]([CH3:35])[S:34][C:30]=2[C:29](=[O:38])[CH:28]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[C:36](=[O:37])[C:31]3[N:32]=[C:33]([CH3:35])[S:34][C:30]=3[C:29](=[O:38])[CH:28]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 673934555-[(3-Bromopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione

Product 1

HCID 673938865-({3-[(4-Methoxybenzyl)amino]propyl}amino)-2-methyl-1,3-benzothiazole-4,7-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

160 μl (1.22 mmol; 1.1 equivalent) of 4-methoxybenzylamine, 213 μl (1.22 mmol; 1.1 equivalent) of diisopropylethylamine and a spatula tip's worth of sodium iodide are added to 0.35 g (1.11 mmol) of 5-[(3-bromopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione in solution in 15 ml of dimethylformamide. The reaction mixture is maintained under stirring under microwaves for 5 minutes at 180° C. Then the solvent is evaporated off under reduced pressure and the reaction residue is taken up in dichloromethane, followed by washing with 3 times 50 ml of water. The organic phases are combined, dried over magnesium sulphate and the solvent is evaporated off under reduced pressure. The expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 95/5) and obtained in the form of a red oil.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customThen the solvent is evaporated off under reduced pressure
  3. washby washing with 3 times 50 ml of water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 95/5)
  7. customobtained in the form of a red oil

Sources & evidence

ORD record
ord-292bb505896a4753b0853485890f267b
Source dataset
uspto-grants-2011_09
Patent number
US08017637B2

Reaction notes

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