Benzyl Bromide → HCID 22100962, compound

HRID 1457820Notes

Reaction equation

HRID 1457820 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:16]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+]>>[CH2:17]([N:13]1[CH2:12][CH:11]=[C:10]([C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][C:6]=3[N:7]=2)[CH2:15][CH2:14]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 128554665-Chloro-2-(pyridin-4-yl)-1,3-benzothiazole

Product 1

HCID 22100962HCID 22100962, compoundYield 66%

Procedure

4-(5-Chlorobenzothiazol-2-yl)pyridine (1.8 g, 7.3 mmol) was reacted with benzyl bromide (1.3 ml, 10.95 mmol), followed by sodium borohydride (361 mg, 9.5 mmol) as exemplified in Example 7 step 2. 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 pale yellow solid (1.63 g, 66%); (Found: C, 66.83; H, 5.00; N, 8.20. C19H17ClN2S requires C, 66.95; H, 5.03; N, 8.22%). δH (CDCl3), 2.76 (4H, m, CH2), 3.24 (2H, m, CH2), 3.67 (2H, s, NCH2Ar), 6.70 (1H, m, NCH2CH), 7.32 (5H, m, ArH), 7.71 (1H, d, J 8.5Hz, ArH), 7.95 (1H, d, J 1.9Hz, ArH). m/z (ES+) 341 (M+1)+.

Workup

  1. customThe crude product was purified by flash chromatography
  2. washeluting with 15% ethyl acetate in petroleum ether
  3. customto give a solid
  4. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-f3889599f8f44f7e854b521cde707b67
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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