Sodium Hydroxide → HCID 23383163, compound

HRID 1281688Notes

Reaction equation

HRID 1281688 reaction equation
C([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[N:11]1[C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[N:13]=[C:12]1Br)(=O)C.[CH:23]1([NH2:26])[CH2:25][CH2:24]1.[OH-].[Na+]>C(O)C>[Cl:20][C:18]1[C:17]([Cl:21])=[CH:16][C:15]2[N:11]([C@@H:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]3[OH:4])[C:12]([NH:26][CH:23]3[CH2:25][CH2:24]3)=[N:13][C:14]=2[CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 70144068HCID 70144068, compound

Product 1

HCID 23383163HCID 23383163, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)trans-2-(2-Bromo-5,6-dichloro-1H-benzimidazol-1-yl)cyclohexyl acetate (Example 45, part c, 1.00 g, 2.46 mmol) and cyclopropylamine (5.0 ml) were refluxed in absolute ethanol (15 ml) for 3 days. The solution was cooled and 1 N sodium hydroxide (2.4 ml) was added. The residual solid was crystallized from ethanol-water to provide title compound as off-white powder (0.56 g, 67%), m.p. 149-151° C.; 1H-NMR (DMSO-d6, 200 MHz) δ: 7.55, 7.39 (both s, each 1, 2 aromatic CH), 6.90 (m, 1, NH), 4.73 (d, J=5.2 Hz, 1, OH), 4.1-3.8 (m, 2, OCH and NCH), 2.8-2.65 (m, 1, CHNH), 2.2-1.9 and 1.8-1.2 (m, 8, 4 CH2), 0.75-0.45 (m, 4, 2 cyclopropyl CH2).

Workup

  1. temperatureThe solution was cooled
  2. customThe residual solid was crystallized from ethanol-water

Sources & evidence

ORD record
ord-93adaf637a93449f9b015cce5cf3e04d
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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