Hydrochloric Acid → HCID 23383162, compound

HRID 1281684Notes

Reaction equation

HRID 1281684 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH:14]12[O:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]2.Cl>CN(C)C=O>[Cl:11][C:10]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([C@@H:14]3[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]3[OH:20])[CH:7]=[N:6][C:5]=2[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9246Cyclohexene oxideHCID 24758Sodium hydrideHCID 3317755,6-Dichloro-1H-benzimidazole

Product 1

HCID 23383162HCID 23383162, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,6-Dichlorobenzimidazole (Townsend and Revankar, Chem. Rev. 1970, 70:389, and references cited therein) (5.00 g, 26.0 mmol) was dissolved in N,N-dimethylformamide (65 ml) and sodium hydride (60% oil dispersion, 50 mg) was added. The solution was heated to 145° and cyclohexene oxide (Aldrich, 7.8 g, 26 mmol) was added in 3 portions over 3 hours. The solution was neutralized with 1 N hydrochloric acid, and evaporated to a purple solid. The solid was recrystallized from ethanol to give title compound as pink crystals (12.55 g, 88%); m.p. 236-238° C.

Workup

  1. temperatureThe solution was heated to 145°
  2. customevaporated to a purple solid
  3. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-e0635367c0454c4781d7692acc8d86b2
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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