Triethylamine → 5-[(3-Bromopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione

HRID 908671Notes

Reaction equation

HRID 908671 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].C(N(CC)CC)C.CO[C:16]1[C:25](=[O:26])[C:20]2[N:21]=[C:22]([CH3:24])[S:23][C:19]=2[C:18](=[O:27])[CH:17]=1>CO>[Br:2][CH2:3][CH2:4][CH2:5][NH:6][C:16]1[C:25](=[O:26])[C:20]2[N:21]=[C:22]([CH3:24])[S:23][C:19]=2[C:18](=[O:27])[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 787013-Bromopropylamine hydrobromideHCID 4817565-Methoxy-2-methylbenzo[d]thiazole-4,7-dione

Product 1

HCID 673934555-[(3-Bromopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1.57 g (7.17 mmol; 1.5 equivalent) of 3-bromopropylamine hydrobromide and 1.02 ml (7.17 mmol; 1.5 equivalent) of triethylamine are added to 1 g (4.78 mmol) of 5-methoxy-2-methyl-1,3-benzothiazole-4,7-dione in solution in 100 ml of methanol. The reaction mixture is maintained under stirring for 2 hours at 60° C., then the solvent is evaporated off under reduced pressure and the residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 97/3). The 5-[(3-bromopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione is obtained in the form of a red oil.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customthe solvent is evaporated off under reduced pressure
  3. customthe residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 97/3)

Sources & evidence

ORD record
ord-b9043b773b5c4588894fef0a83f1752a
Source dataset
uspto-grants-2011_09
Patent number
US08017637B2

Reaction notes

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