2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-(Benzoxazol-2-yl)-1-(cyclohexanon-4-yl)-2-methylbenzimidazole

HRID 74250Notes

Reaction equation

HRID 74250 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:26]=[CH:25][C:13]2[N:14]([CH:18]3[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]3)[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:26]=[CH:25][C:13]2[N:14]([CH:18]3[CH2:19][CH2:20][C:21](=[O:24])[CH2:22][CH2:23]3)[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 674984805-(Benzoxazol-2-yl)-1-(4-hydroxycyclohexyl)-2-methylbenzimidazole

Product 1

HCID 674977695-(Benzoxazol-2-yl)-1-(cyclohexanon-4-yl)-2-methylbenzimidazoleYield 41.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-1-(4-hydroxycyclohexyl)-2-methylbenzimidazole (see Working Example 49-2) (50 mg, 0.14 mmol) in chloroform (3 mL) was added DDQ (35 mg, 0.16 mmol), and this was stirred overnight at room temperature. After the reaction was complete, this was concentrated, and the residue obtained was purified by silica gel column chromatography to yield the title compound (20 mg, 40% yield) as reddish-brown crystals.

Workup

  1. concentrationthis was concentrated
  2. customthe residue obtained
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c577cbb04c534bcf911d1d14ceb4a341
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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