alpha-Bromo-o-chlorotoluene → HCID 22100965, compound

HRID 1457817Notes

Reaction equation

HRID 1457817 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:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]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]([CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[Cl:17])[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 11905alpha-Bromo-o-chlorotolueneHCID 22100974HCID 22100974, compound

Product 1

HCID 22100965HCID 22100965, compoundYield 44%

Procedure

4-(Benzothiazol-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (200 mg, 0.8 mmol) was reacted with 2-chlorobenzyl bromide (0.13 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 yellow solid (120 mg, 44%). (Found: C, 65.13; H, 4.72; N, 7.33. C19H17ClN2S. 0.5H2O requires C, 65.22; H, 5.19; N, 8.01%). δH (CDCl3), 2.84 (4H, m, CH2), 3.33 (2H, m, NCH2CH2), 3.80 (2H, s, NCH2Ar), 6.70 (1H, m, NCH2CH), 7.41 (6H, m, ArH), 7.82 (1H, d, J 7.8Hz, 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-15a4fc3e2f7d4c648d8e2101d6b9f36a
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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