1-(Bromomethyl)-3-chlorobenzene → HCID 22100943, compound

HRID 1457816Notes

Reaction equation

HRID 1457816 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.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br>>[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]([CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[CH:19]=2)[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 22100974HCID 22100974, compound

Product 1

HCID 22100943HCID 22100943, compoundYield 45%

Procedure

4-(Benzothiazol-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (200 mg, 0.8 mmol) was reacted with 3-chlorobenzyl bromide (0.1 ml, 0.8 mmol) as exemplified in Example 1. The crude product was purified by flash chromatography eluting with 15% ethyl acetate in petroleum ether to give the title compound as a pale yellow solid (120 mg, 45%); (Found: C, 65.57; H, 4.87; N, 7.59. C19H17ClNS. 0.5H2O requires C, 65.22; H, 5.19; N, 8.01%). δH (CDCl3), 2.77 (2H, m, NCH2 CH2), 2.84 (2H, m, NCH2CH2), 3.24 (2H, m, NCH2 CH2), 3.65 (2H, s, NCH2Ar), 6.68 (1H, m, NCH2CH), 7.25 (2H, s, ArH), 7.36 (4H, m, ArH), 7.82 (1H, d, J 8.0Hz, ArH), 7.98 (1H, d, J 8.1Hz, 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

Sources & evidence

ORD record
ord-8c342c79913244ffa4ab90e00ebc3ce3
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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