5,6-Dimethylbenzimidazole → HCID 86681092, compound

HRID 1848119Notes

Reaction equation

HRID 1848119 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]([CH3:13])=[CH:11][C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=1.Cl[CH2:15][C:16]1[CH:26]=[CH:25][C:19]2[N:20]=[C:21]([S:23][CH3:24])[S:22][C:18]=2[CH:17]=1>CN(C=O)C>[CH3:3][C:4]1[C:12]([CH3:13])=[CH:11][C:7]2[N:8]([CH2:15][C:16]3[CH:26]=[CH:25][C:19]4[N:20]=[C:21]([S:23][CH3:24])[S:22][C:18]=4[CH:17]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6755,6-DimethylbenzimidazoleHCID 24758Sodium hydrideHCID 866809946-(Chloromethyl)-2-(methylthio)benzo[d]thiazole

Product 1

HCID 86681092HCID 86681092, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of anhydrous DMF (15 mL) and sodium hydride (60% dispersion in mineral oil, 105 mg, 2.63 mmol) at 0° C. under nitrogen, was added portionwise 5,6-dimethyl-1H-benzo[d]imidazole (215 mg, 1.4 mmol). The reaction mixture was stirred for 5 min. A solution of 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (320 mg, 1.4 mmol) from Step 4 of Example 36 in anhydrous DMF (2 mL) was added dropwise. The reaction mixture was allowed to warm to rt and stir for 1 h. The reaction solution was poured into ice-water and extracted with EtOAc (50 mL×3). The combined organic layers were further washed with water (20 mL), then brine (20 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 6-((5,6-dimethyl-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (450 mg, 96%) as a yellow solid which was not purified further. 1H NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.59 (s, 1H), 7.46 (s, 1H), 7.24-7.26 (m, 1H), 7.03 (s, 1H), 5.40 (s, 2H), 2.77 (s, 3H), 2.37 (s, 3H), 2.32 (s, 3H); LCMS (ESI) m/z 340 (M+H)+.

Workup

  1. stirringstir for 1 h
  2. extractionextracted with EtOAc (50 mL×3)
  3. washThe combined organic layers were further washed with water (20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-325b25de3f2342079c388d558dbf6e60
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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