Hydrochloric Acid → 4-bromo-1-(3-chloro-2-methylbenzyl)-1H-benzo[d]imidazol-6-amine

Temperature

80 °C

To a solution of 4-bromo-1-(3-chloro-2-methylbenzyl)-6-nitro-1H-benzo[d]imidazole (3.05 g, 8.01 mmol) in Methanol (35 mL) in a 250 ml round bottomed flask was added Tin(II)chloride dihydrate (10.85 g, 48.1 mmol) and HCl (2.19 mL, 72.1 mmol). The reaction mixture was left to stir at 80° C. for 1 h. The solvent was removed and diluted with water (100 mL) and this solution was decanted into a 250 mL Erlenmeyer flask. The brown residue in the round bottomed flask was dissolved in 100 mL of EtOAc and washed with 1N NaOH, brine, dried and evaporated to yield a brown solid. The water layer was extracted with EtOAc, washed with 1N NaOH, brine, dried (MgSO4) and evaporated to a brown solid. The solids found to be identical by 1 cms and were combined to yield a brown solid 4-bromo-1-(3-chloro-2-methylbenzyl)-1H-benzo[d]imidazol-6-amine (2.33 g, 6.64 mmol, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.40 (s, 3H) 5.45 (s, 2H) 6.47 (d, J=1.52 Hz, 1H) 6.56 (d, J=7.58 Hz, 1H) 6.86 (d, J=1.52 Hz, 1H) 7.14 (s, 1H) 7.39 (d, J=7.83 Hz, 1H) 8.11 (s, 1H); LC/MS: MS (ES+) m/e 351 [M+H]+.

1. waitThe reaction mixture was left
2. customThe solvent was removed
3. additiondiluted with water (100 mL)
4. customthis solution was decanted into a 250 mL Erlenmeyer flask
5. dissolutionThe brown residue in the round bottomed flask was dissolved in 100 mL of EtOAc
6. washwashed with 1N NaOH, brine
7. customdried
8. customevaporated
9. customto yield a brown solid
10. extractionThe water layer was extracted with EtOAc
11. washwashed with 1N NaOH, brine
12. dry with materialdried (MgSO4)
13. customevaporated to a brown solid

ORD record

ord-9d72d2a923634b17a6903818d2147364

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778937B2