Sodium hydride → HCID 15841143, compound

HRID 260647Notes

Reaction equation

HRID 260647 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Cl[C:17]1[CH:26]=[N:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[Cl:27])[N:18]=1>O>[Cl:27][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:24]=1[N:25]=[CH:26][C:17]([NH:13][S:10]([C:8]1[CH:7]=[CH:6][C:5]3[O:1][CH:2]=[CH:3][C:4]=3[CH:9]=1)(=[O:11])=[O:12])=[N:18]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 106794872,5-dichloroquinoxalineHCID 15841151HCID 15841151, compound

Product 1

HCID 15841143HCID 15841143, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a manner similar to Example 4, the reaction mixture from benzofuran-5-sulfonamide (397 mg, 2.01 mmol), sodium hydride (60%, 315 mg, 7.9 mmol) and 2,5-dichloroquinoxaline (600 mg, 3.01 mmol) was poured carefully into water and washed with hexanes. The hexane-free aqueous was acidified to a pH of 1-2 by the addition of 5N hydrochloric acid solution and the resulting precipitate was collected and dried. This precipitate was washed with methylene chloride and the solid obtained by evaporation of the filtrate was purified by radial silica gel chromatography (EtOAc/hexanes) followed by silica gel flash chromatography (diethyl ether/hexanes). The resulting foam which was broken up in hexanes, collected and dried, finally under vacuum at 80° C. to yield the title product (110 mg, 15%) as a solid.

Workup

  1. washwashed with hexanes
  2. additionThe hexane-free aqueous was acidified to a pH of 1-2 by the addition of 5N hydrochloric acid solution
  3. customthe resulting precipitate was collected
  4. customdried
  5. washThis precipitate was washed with methylene chloride
  6. customthe solid obtained by evaporation of the filtrate
  7. customwas purified by radial silica gel chromatography (EtOAc/hexanes)
  8. customcollected
  9. customdried, finally under vacuum at 80° C.

Sources & evidence

ORD record
ord-ae1ca73b6971456db017e41888908628
Source dataset
uspto-grants-1996_06
Patent number
US05529999

Reaction notes

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