Bromine → HCID 15171531, compound

HRID 728130Notes

Reaction equation

HRID 728130 reaction equation
C([NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][CH3:23])=[S:21])=[CH:15][CH:14]=2)[CH:8]=[CH:7][N:6]=1)(=O)C.BrBr>C(Cl)(Cl)Cl>[NH2:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]3[N:19]=[C:20]([NH:22][CH3:23])[S:21][C:15]=3[CH:14]=2)[CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 15171495HCID 15171495, compound

Product 1

HCID 15171531HCID 15171531, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-acetamido-4-[2-{4-(3-methylthioureido)phenyl}ethyl]pyrimidine (5.8 g) in chloroform (100 ml) was dropwise added a solution of bromine (3.1 g) in chloroform (3 ml) at ambient temperature under stirring and the mixture was stirred at the same temperature for one hour. Further, the resultant mixture was refluxed for 2 hours with stirring. 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 8.0 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 column was eluted with a mixture of ethyl acetate and tetrahydrofuran (9:1 V/V), and the fraction containing the desired product was evaporated in vacuo and the crystalline residue was washed with ethyl acetate to give 6-[2-(2-amino-4-pyrimidinyl)ethyl]-2-methylaminobenzothiazole (0.66 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for one hour
  2. stirringwith stirring
  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 column was eluted with a mixture of ethyl acetate and tetrahydrofuran (9:1 V/V)
  11. additionthe fraction containing the desired product
  12. customwas evaporated in vacuo
  13. washthe crystalline residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-7d529daa8f174e938660b5124ddc30f6
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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