Sodium hydride → HCID 70196834, compound

HRID 583339Notes

Reaction equation

HRID 583339 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[H-].[Na+].[CH:26]1[CH:31]=[C:30]([CH2:32]Br)[C:29]([CH2:34]Br)=[CH:28][CH:27]=1>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3]([C:4]1[C:5]2[N:11]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)(=[O:13])=[O:14])[CH2:32][C:30]3[CH:31]=[CH:26][CH:27]=[CH:28][C:29]=3[CH2:34][O:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:23]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 66665o-Bis(bromomethyl)benzeneHCID 54048961HCID 54048961, compound

Product 1

HCID 70196834HCID 70196834, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.350 g (1.039 mmol) of the product of Example 31 in 35 mL of DMF was added 0.104 g (2.596 mmol) of 60% sodium hydride and the solution was stirred at room temperature for 15 minutes. To the resulting mixture was then added 0.384 g (1.454 mmol) of a,a'-dibromo-o-xylene and the reaction mixture was then heated to 80° C. for 18 h, cooled to room temperature, diluted with ether and washed with water. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel eluting with EtOAc/hexanes (1:3) to provide 0.358 g (79%) of the desired product as a white solid. Electrospray Mass Spec: 440 (M+H).

Workup

  1. temperaturethe reaction mixture was then heated to 80° C. for 18 h
  2. temperaturecooled to room temperature
  3. washwashed with water
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was chromatographed on silica gel eluting with EtOAc/hexanes (1:3)

Sources & evidence

ORD record
ord-cf0f04c8403a4d20b1d9aac69100d8e4
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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