Bromine → HCID 10400895, compound

HRID 728128Notes

Reaction equation

HRID 728128 reaction equation
[CH3:1][NH:2][C:3](=[S:19])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][CH:6]=1.BrBr>C(Cl)(Cl)Cl>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]2[N:4]=[C:3]([NH:2][CH3:1])[S:19][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 9970424HCID 9970424, compound

Product 1

HCID 10400895HCID 10400895, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-[2-{4-(3-methylthioureido)phenyl}ethyl]pyridine (7.1 g) in chloroform (100 ml) was dropwise added a bromine (4.6 g) at ambient temperature under stirring and the mixture was stirred at the same temperature for one hour. Further, the resultant mixture was refluxed under stirring for hours. The reaction mixture was evaporated in vacuo and the residue was heated with 10% hydrochloric acid (100 ml) for one hour at 70° to 80° C. The resultant mixture was washed with ethyl acetate. The separated aqueous layer was adjusted to pH 7.5 with aqueous 20% potassium carbonate and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on silica gel. The fraction eluted with a mixture of ethyl acetate and diisopropyl ether (6:4 V/V) was collected and solvent was evaporated in vacuo to give a crystalline residue of 6-[2-(2-pyridyl)ethyl]-2-methylaminobenzothiazole (1.0 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for one hour
  2. stirringunder stirring for hours
  3. customThe reaction mixture was evaporated in vacuo
  4. temperaturethe residue was heated with 10% hydrochloric acid (100 ml) for one hour at 70° to 80° C
  5. washThe resultant mixture was washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated in vacuo
  10. washThe fraction eluted with a mixture of ethyl acetate and diisopropyl ether (6:4 V/V)
  11. customwas collected
  12. customsolvent was evaporated in vacuo

Sources & evidence

ORD record
ord-cc401f37b7c949fa9a6e22f227012b6e
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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