Benzyl Bromide → HCID 22100940, compound

HRID 1457814Notes

Reaction equation

HRID 1457814 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CN(C=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 236319benzothiazole, 2-(4-pyridinyl)-HCID 4311764Sodium borohydride

Product 1

HCID 22100940HCID 22100940, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(Benzothiazol-2-yl)pyridine (4.5 g, 0.02 mol) was suspended in DMF (10 ml) and benzyl bromide (3.8 ml, 0.03 mol) added and the reaction mixture stirred at reflux for 1 hour. On cooling, the solid was filtered and washed with ether (20 ml). The solid was then suspended in ethanol (100 ml), sodium borohydride (1.05 g, 0.026 mol) added and the reaction stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, the residue diluted with water (50 ml) and the product extracted into dichloromethane (3×50 ml). The combined organic layers were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by flash chromatography eluting with 15% ethyl acetate in petroleum ether to give a solid. Recrystallisation from ethyl acetate afforded the title compound as a white solid (4.1 g, 67%); (Found: C, 74.31; H, 5.87; N, 9.07. C19H18N2S requires C, 74.47; H, 5.92; N, 9.14%). δH (CDCl3), 2.76 (2H, m, NCH2 CH2), 2.83 (2H, m, NCH2CH2), 3.23 (2H, m, NCH2 CH2), 3.67 (2H, s, NCH2Ph), 6.67 (1H, m, NCH2CH), 7.35 (7H, m, ArH), 7.81 (1H, d, J 7.9Hz, ArH), 7.97 (1H, d, J 8.1Hz, ArH). m/z (ES+) 307 (M+1)+.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureOn cooling
  3. filtrationthe solid was filtered
  4. washwashed with ether (20 ml)
  5. stirringthe reaction stirred at room temperature overnight
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. additionthe residue diluted with water (50 ml)
  8. extractionthe product extracted into dichloromethane (3×50 ml)
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customThe crude product was purified by flash chromatography
  13. washeluting with 15% ethyl acetate in petroleum ether
  14. customto give a solid
  15. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-b6c4dbc84bd3445aa7a767e33f5cbb1e
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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