Pyridine → HCID 70145021, compound

HRID 1281685Notes

Reaction equation

HRID 1281685 reaction equation
[Cl:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]2[N:6]([C@@H:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]3[OH:15])[CH:7]=[N:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([O:15][C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]1[N:6]1[C:5]2[CH:16]=[C:17]([Cl:18])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=[CH:7]1)(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23383162HCID 23383162, compound

Product 1

HCID 70145021HCID 70145021, compoundYield 97%

Procedure

(±)-trans-2-(5,6-Dichloro-1H-benzimidazol-1-yl)cyclohexanol (part a of this example, 6.25 g, 21.9 mmol) was stirred in acetic anhydride (3 ml)-pyridine (50 ml) for 18 h. Volatiles were evaporated and the residue partitioned between chloroform and saturated aqueous sodium bicarbonate. The chloroform solution was filtered through Celite/charcoal and evaporated to give title compound as an off-white solid (6.92 g, 97%), m.p. 145-147° C.

Workup

  1. customfor 18 h
  2. customVolatiles were evaporated
  3. customthe residue partitioned between chloroform and saturated aqueous sodium bicarbonate
  4. filtrationThe chloroform solution was filtered through Celite/charcoal
  5. customevaporated

Sources & evidence

ORD record
ord-4610d81bd82245c2b48171e28f46354a
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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