Bromine → HCID 20228686, compound

HRID 1731355Notes

Reaction equation

HRID 1731355 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][CH3:21])=[S:19])=[CH:13][CH:12]=3)[N:10]=[C:4]2[CH:3]=1.[Br:22]Br>C(Cl)(Cl)Cl>[Br:22][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]2=[N:10][C:9]=1[C:11]1[CH:12]=[CH:13][C:14]2[N:17]=[C:18]([NH:20][CH3:21])[S:19][C:15]=2[CH:16]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 20228706HCID 20228706, compound

Product 1

HCID 20228686HCID 20228686, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
82.5 °C

Procedure

To a solution of 7-methyl-2-[4-(3-methylthioureido)phenyl]imidazo[1,2-a]pyridine (9.0 g) in chloroform (300 ml) was added portionwise bromine (11.5 g) at ambient temperature and the mixture was refluxed for 6 hours under stirring. The reaction mixture was evaporated in vacuo. To the residue was added 5% hydrochloric acid (300 ml) and the mixture was heated at 80 to 85° C. for 5 hours. The reaction mixture was filtered and the filtrate was adjusted to pH 7.5 with 20% potassium carbonate. From the resultant aqueous solution the product was extracted with a mixture of ethyl acetate and tetrahydrofuran. The organic 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 eluting with a mixture of ethyl acetate and tetrahydrofuran (8:2) and the fraction containing the desired compound was evaporated in vacuo to give 6-(3-bromo-7-methyl imidazo[1,2-a]pyridin-2-yl)- 2-methylaminobenzothiazole (1.7 g). mp. 225° C. (dec.).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. additionTo the residue was added 5% hydrochloric acid (300 ml)
  4. filtrationThe reaction mixture was filtered
  5. extractionFrom the resultant aqueous solution the product was extracted with a mixture of ethyl acetate and tetrahydrofuran
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated in vacuo
  10. additionthe residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and tetrahydrofuran (8:2)
  11. additionthe fraction containing the desired compound
  12. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-071e2fa9ec184942a2753a88923e2bca
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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