Bromine → HCID 10126310, compound

HRID 51841

Reaction equation

HRID 51841 reaction equation
[C:1]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([N:19]([CH2:21][CH2:22][O:23][CH3:24])[CH3:20])[CH:16]=[CH:15][C:14]=1[O:25][CH3:26])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr>C(Cl)(Cl)Cl>[CH3:26][O:25][C:14]1[C:13]2[N:12]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:11][C:18]=2[C:17]([N:19]([CH2:21][CH2:22][O:23][CH3:24])[CH3:20])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 220157361-Benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea

Product 1

HCID 10126310HCID 10126310, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 430 mg (1.15 mmol) 1-benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea in 8 ml chloroform was added dropwise 0.059 ml (1.15 mmol) bromine and the reaction mixture heated at reflux for 18 hours. The mixture was then cooled to room temperature, poured slowly onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/4 ethyl acetate/hexane) afforded 120 mg (28%) N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide as a yellow solid. ES-MS m/e (%): 394 (M+Na+, 14), 372 (M+H+, 100).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 18 hours
  3. additionpoured slowly onto water
  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-a61b9c3d8d1b4f1790842e33b95a037d
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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