5,6-dichloro-1,2-dimethylbenzimidazole → HCID 178471416, compound

HRID 1020891Notes

Reaction equation

HRID 1020891 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[CH:11][C:5]2[N:6]([CH3:10])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.[F:14][C:15]([F:31])([F:30])[S:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:18])=[O:17]>ClCCl>[F:14][C:15]([F:31])([F:30])[S:16]([O-:19])(=[O:18])=[O:17].[Cl:13][C:12]1[C:2]([Cl:1])=[CH:3][C:4]2[N+:8]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:7]([CH3:9])[N:6]([CH3:10])[C:5]=2[CH:11]=1

Participants

4

Reactant 2

HCID 8407155,6-dichloro-1,2-dimethylbenzimidazoleHCID 10517725HCID 10517725, compound

Product 1

HCID 178471416HCID 178471416, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2 (2 g, 1 eq) in 10 mL dichloromethane was added 4 (2.8 g, 1 eq) and stirred in dark for 24 hrs at room temperature. Solvent was evaporated under reduced pressure and the residue was recrystalized from MeOH/diethyl ether to get the white powder as product (4.1 g, 87% yield.) See FIG. 11. 1H NMR: (DMSO) 1.16 (t, 3H), 1.37 (m, 2H), 1.57 (m, 2H), 1.75 (m, 2H), 2.28 (t, 2H), 2.88 (s, 3H), 3.96 (s, 3H), 4.04 (q, 2H), 4.46 (t, 2H), 8.48 (s, 1H), 8.52 (s, 1H). 13C NMR: (DMSO): 10.61, 13.98, 23.90, 25.04, 28.11, 31.98, 33.20, 45.09, 59.58, 114.73, 114.78, 128.76, 128.79, 130.06, 130.91, 154.24, 172.63. ESI-MS (m/z) calcd (found): 357.1 (357.3) for [M]+.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe residue was recrystalized from MeOH/diethyl ether
  3. customto get the white powder as product (4.1 g, 87% yield.)

Sources & evidence

ORD record
ord-98c252f7a5984679961a4ea6b17d2658
Source dataset
uspto-grants-2014_05
Patent number
US08716491B2

Reaction notes

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