4-(Bromomethyl)benzonitrile → HCID 22100953, compound

HRID 1457818Notes

Reaction equation

HRID 1457818 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1>>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH2:12][CH2:13][N:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 22100974HCID 22100974, compound

Product 1

HCID 22100953HCID 22100953, compoundYield 60.3%

Procedure

4-(Benzothiazol-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (300 mg, 1.2 mmol) was reacted with α-bromo-p-tolunitrile (280 mg, 1.44 mmol) as exemplified in Example 1. The crude product was purified by flash chromatography eluting with 25% ethyl acetate in petroleum spirit to give a solid. Recrystallisation of this solid from ethyl acetate yielded the title compound as a yellow solid (240 mg, 60%) mp. 165°-166° C. (Found: C, 72.00; H, 4.92; N, 12.61. C20H17N3S requires C, 72.48; H, 5.17; N, 12.68%). δH (CDCl3), 2.76 (2H, m, NCH2CH2), 2.83 (2H, m, NCH2CH2), 3.24 (2H, m, NCH2CH2), 3.72 (2H, s, NCH2Ar), 6.68 (1H, m, NCH2CH), 7.41 (4H, m, ArH), 7.51 (1H, d, J 8.4Hz, ArH), 7.64 (1H, d, J 8.4Hz, ArH), 7.83 (1H, d, J 7.0Hz, ArH), 8.00 (1H, d, J 8.3Hz, ArH). m/z (ES+) 332 (M+1)+.

Workup

  1. customThe crude product was purified by flash chromatography
  2. washeluting with 25% ethyl acetate in petroleum spirit
  3. customto give a solid
  4. customRecrystallisation of this solid from ethyl acetate

Sources & evidence

ORD record
ord-ef667b606d1e448fa60e0fbd7df2b616
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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