Sodium Hydroxide → HCID 19926453, compound

HRID 1647154Notes

Reaction equation

HRID 1647154 reaction equation
[C:1]([C:4]1[C:31]([CH3:32])=[CH:30][C:7]2[NH:8][C:9]([S:11][CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH2:22][C:23]4([CH3:29])[CH2:28][O:27][CH2:26][O:25][CH2:24]4)[CH:16]=[CH:15][N:14]=3)=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].C([O-])(O)=[O:34].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+]>C(Cl)Cl.O>[C:1]([C:4]1[C:31]([CH3:32])=[CH:30][C:7]2[NH:8][C:9]([S:11]([CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH2:22][C:23]4([CH3:29])[CH2:24][O:25][CH2:26][O:27][CH2:28]4)[CH:16]=[CH:15][N:14]=3)=[O:34])=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19926457HCID 19926457, compound

Product 1

HCID 19926453HCID 19926453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 5-acetyl-6-methyl-2-[[(3-methoxy-4-(5-methyl-1,3-dioxan-5-yl-methoxy)-2-pyridinyl)methyl]thio]-1H-benzimidazole (87 mg, 0.19 mmol) in 20 ml CH2Cl2 and NaHCO3 (32 mg, 0.38 mmol) in 5 ml H2O was cooled to 0° C. and treated with 3-chloro-perbenzoic acid (47 mg 70%, 0.19 mmol). After reacting for 10 min the layers were separated (the aqueous layer was washed once more with 5 ml CH2Cl2) and the organic layer extracted with 10 ml H2O containing NaOH (15 mg, 38 mmol). The alkaline aqueous layer was collected and treated with several portions of methyl formate (each 23 μl, 38 mmol) until the solution turned opaque. The aqueous layer was extracted with 25+10 ml CH2Cl2. The two latter organic layers were combined, dried over MgSO4 and evaporated. The residue was chromatographed (SiO2, CH2Cl2 /MeOH saturated with NH3(g), 93/7) yielding 40 mg (44%) pure solfoxide.

Workup

  1. customthe layers were separated (the aqueous layer
  2. washwas washed once more with 5 ml CH2Cl2) and the organic layer
  3. extractionextracted with 10 ml H2O
  4. customThe alkaline aqueous layer was collected
  5. additiontreated with several portions of methyl formate (each 23 μl, 38 mmol) until the solution
  6. extractionThe aqueous layer was extracted with 25+10 ml CH2Cl2
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe residue was chromatographed (SiO2, CH2Cl2 /MeOH saturated with NH3(g), 93/7)
  10. customyielding 40 mg (44%) pure solfoxide

Sources & evidence

ORD record
ord-ff203e3621ff44cfb252a2756a077cde
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

Loading…