Ammonia → HCID 23383155, compound

HRID 1281687Notes

Reaction equation

HRID 1281687 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]1[Br:22])(=O)C.N>CO>[Br:22][C:12]1[N:11]([C@@H:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]2[OH:4])[C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[N:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 70144068HCID 70144068, compound

Product 1

HCID 23383155HCID 23383155, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-Trans-2-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)cyclohexyl acetate (part c of this example, 500 mg, 1.23 mmol) was dissolved in methanol half-saturated with ammonia (at 0° C.) and the solution stirred at room temperature for 18 hours. Volatiles were evaporated and the residual solid recrystallized from methanol-water to give title compound as white crystals (350 mg, 78%), m.p. 186-188° C.; 1H-NMR (DMSO-d6, 200 MHz) δ: 8.23, 7.93 (both s, each 1, 2 aromatic CH), 4.99 (d, J=4.7 Hz, 1, OH), 4.34.1 (m, 2, OCH and NCH), 2.4-1.3 (m, 8, 4CH2).

Workup

  1. customVolatiles were evaporated
  2. customthe residual solid recrystallized from methanol-water

Sources & evidence

ORD record
ord-d24b9f8b24b24a27a435f0e9ffd3c0c8
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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