4-(Bromomethyl)-1,2-dichlorobenzene → HCID 178526488, compound

HRID 2292649Notes

Reaction equation

HRID 2292649 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9]([SH:11])=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18]Br>C(O)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18][S:11][C:9]1[NH:8][C:7]2[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[N:10]=1

Participants

4

Reactant 2

HCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 178526489HCID 178526489, compound

Product 1

HCID 178526488HCID 178526488, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-nitro-1H-benzoimidazol-2-thiol (1.95 g, 0.01 mol) and 3,4-dichlorobenzylbromide (2.4 g, 0.01 mol) was heated at reflux in ethanol (100 mL) for a period of 20 hours. The mixture was then concentrated. The solid was collected by filtration. The solid was dissolved in a mixture of EtOAc/H2O. Sodium bicarbonate was added until basic. The organic phase was separated and the solvent evaporated. The residue was dissolved in ethanol. The solution was saturated with hydrogen chloride. The solution was then concentrated to the precipitation point. The solid was then collected to give the title compound (2.3 g, 59% yield) as a mono-hydrochloride, off-white solid, m.p. 232°-234° C. (dec.). Mass spectrum (EI; M+) m/z 353/355/347. Anal. Calcd. for C14H9Cl2N3O2 S.HCl: C, 43.04; H, 2.58; N, 10.76. Found: C, 43.24; H, 2.47; N, 10.69. 1H-NMR (DMSO-d6 ; 400 MHz): δ 8.32 (s, 1H), 8.07 (d, 1H), 7.78 (s, 1H), 7.62 (d, 1H), 7.56 (d, 1H), 7.49 (d, 1H), and 4.64 ppm (s, 2H).

Workup

  1. temperaturewas heated
  2. concentrationThe mixture was then concentrated
  3. filtrationThe solid was collected by filtration
  4. dissolutionThe solid was dissolved in a mixture of EtOAc/H2O
  5. additionSodium bicarbonate was added until basic
  6. customThe organic phase was separated
  7. customthe solvent evaporated
  8. dissolutionThe residue was dissolved in ethanol
  9. concentrationThe solution was then concentrated to the precipitation point
  10. customThe solid was then collected

Sources & evidence

ORD record
ord-d974345db5534ccd9b631ca617d681e8
Source dataset
uspto-grants-1997_11
Patent number
US05684030

Reaction notes

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