Diethyl Ether → HCID 10253281, compound

HRID 2181807Notes

Reaction equation

HRID 2181807 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:27]([CH3:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].I[CH2:36][CH3:37].[CH2:38](OCC)[CH3:39]>CN(C)C=O.O>[CH2:38]([O:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:27]([CH3:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:36][CH3:37])=[O:5])[CH3:39]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 10430792HCID 10430792, compound

Product 1

HCID 10253281HCID 10253281, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A stirred suspension of 2-hydroxy-5-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]benzoic acid (0.5 g, 1.26 mmol) and anhydrous potassium carbonate (0.36 g, 2.6 mmol) in anhydrous N,N-dimethylformamide (5 mL) was treated drop-wise at room temperature under nitrogen with a solution of iodoethane (0.405 g, 2.6 mmol) in anhydrous N,N-dimethylformamide (1 mL). The mixture was stirred at room temperature overnight. The reaction was diluted with diethyl ether and water. The organic phase was separated and washed sequentially with a 1 N hydrochloric acid solution and water. After drying over anhydrous sodium sulfate, the organic phase was filtered through a short column of silica gel, and the filtrate evaporated in vacuo to yield a crude product (0.5 g). The crude product was purified by preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with a mixture of methyl tert-butyl ether-hexane (15:85) at a flow rate of 40 mL/min to afford, after evaporation of the solvent, a colorless solid. Crystallization of the colorless solid from a mixture of diethyl ether-hexane yielded the title compound (0.239 g, 0.53 mmol, 42%) as a homogeneous, white powder, m.p. 113-115° C.;

Workup

  1. customThe organic phase was separated
  2. washwashed sequentially with a 1 N hydrochloric acid solution and water
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. filtrationthe organic phase was filtered through a short column of silica gel
  5. customthe filtrate evaporated in vacuo
  6. customto yield a crude product (0.5 g)
  7. customThe crude product was purified by preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g)
  8. washeluting with a mixture of methyl tert-butyl ether-hexane (15:85) at a flow rate of 40 mL/min
  9. customto afford
  10. customafter evaporation of the solvent
  11. customCrystallization of the colorless solid
  12. additionfrom a mixture of diethyl ether-hexane

Sources & evidence

ORD record
ord-2285b141bf8d4272a64e30bc7619720b
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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