Benzyl Bromide → HCID 22100950, compound

HRID 1457822Notes

Reaction equation

HRID 1457822 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:17]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+]>>[CH2:20]([N:14]1[CH2:13][CH:12]=[C:11]([C:9]2[S:10][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:18])([F:1])[F:19])=[CH:17][C:7]=3[N:8]=2)[CH2:16][CH2:15]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 12855467HCID 12855467, compound

Product 1

HCID 22100950HCID 22100950, compoundYield 47%

Procedure

4-(5-Trifluoromethylbenzothiazol-2-yl)pyridine (10 g, 0.04 mol) was reacted with benzyl bromide (6.4 ml, 0.06 mol) followed by sodium borohydride (1.76 g, 0.052 mol) 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 yellow solid. Recrystallisation from ethyl acetate afforded the title compound as a pale yellow solid (7 g, 47%); mp. 124°-125° C.; (Found: C, 63.85; H, 4.48; N, 7.48. C20 H17F3N2S requires C, 64.16; H, 4.58; N, 7.48%). δH (CDCl3), 2.75 (2H, m, NCH2CH2), 2.81 (2H, m, NCH2CH2), 3.24 (2H, m, NCH2CH2), 3.67 (2H, s, NCH2Ar), 6.71 (1H, m, NCH2CH), 7.28 (5H, m, ArH), 7.55 (1H, d of d, J 8.4Hz, J 1.4Hz, ArH), 7.89 (1H, d, J 8.4Hz, ArH), 8.23 (1H, s, ArH); m/z (ES+) 375 (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 yellow solid
  4. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-dd3286d29a15459cb1cd78082d455b88
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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