Sodium Hydroxide → HCID 19996488, compound

HRID 2248438Notes

Reaction equation

HRID 2248438 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([S:22][CH2:23][C:24]3[C:29]([CH3:30])=[C:28]([O:31][CH3:32])[C:27]([CH3:33])=[CH:26][N:25]=3)[NH:18][C:17]=2[CH:16]=[C:15]([CH3:34])[C:14]=1[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[OH-].[Na+]>C(Cl)Cl.O>[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([S:22]([CH2:23][C:24]3[C:29]([CH3:30])=[C:28]([O:31][CH3:32])[C:27]([CH3:33])=[CH:26][N:25]=3)=[O:9])[NH:18][C:17]=2[CH:16]=[C:15]([CH3:34])[C:14]=1[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 19996503HCID 19996503, compound

Product 1

HCID 19996488HCID 19996488, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

m-Chloroperbenzoic acid, 91% (1.13 g, 0.0059 mol) dissolved in CH2Cl2 (25 ml) and cooled to -10° C. was added under stirring to 4,6-dimethyl-5-heptyloxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole (2.7 g, 0.0059 mol) dissolved in CH2Cl2 (50 ml) maintaining the temperature at -5° C. Stirring was continued at -5° C. for 10 min. The two phases were separated and then NaOH (0.26 g, 0.0066 mol) dissolved in water (50 ml) was added under vigorous stirring. The two phases were separated. The organic phase was dried (Na2SO4), filtered and the solvent evaporated off giving a residual oil, which according to NMR included 30% of unreacted starting material. The oil was chromatographed on a silica column using CH3OH--CH2Cl2 5:95 as eluant and then the product was recrystallized from CH3CN giving the desired product in crystalline form (0.85 g, 32%), m.p. 116° C.

Workup

  1. additionwas added
  2. temperaturemaintaining the temperature at -5° C
  3. customThe two phases were separated
  4. additionwas added under vigorous stirring
  5. customThe two phases were separated
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent evaporated off
  9. customgiving a residual oil, which
  10. customThe oil was chromatographed on a silica column
  11. customthe product was recrystallized from CH3CN giving the desired product in crystalline form (0.85 g, 32%), m.p. 116° C.

Sources & evidence

ORD record
ord-0ae1364e2fd9409eb009a38e054b6480
Source dataset
uspto-grants-1991_08
Patent number
US05039806

Reaction notes

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