Bromine → 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine

HRID 51843

Reaction equation

HRID 51843 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:11][CH2:12][O:13][CH3:14])[CH3:10])=[CH:5][C:4]=1[NH:15][C:16]([NH2:18])=[S:17].BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[N:15]=[C:16]([NH2:18])[S:17][C:5]=2[C:6]([N:9]([CH2:11][CH2:12][O:13][CH3:14])[CH3:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 22015743{2-Methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea

Product 1

HCID 220157444-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamineYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1.40 g (5.20 mmol) {2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea in 35 ml chloroform was added dropwise 0.27 ml (5.27 mmol) bromine and the reaction mixture heated at reflux for 18 hours. The mixture was then cooled to room temperature, poured slowly onto sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 984 mg (71%) 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine as an orange crystalline solid. ES-MS m/e (%): 268 (M+H+, 100).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 18 hours
  3. additionpoured slowly onto sodium bicarbonate solution
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a841510e466244a7a8f6cd35137249f7
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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