Sodium hydride → HCID 53901140, compound

HRID 440635Notes

Reaction equation

HRID 440635 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:3]=1[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5].[H-].[Na+].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:7]([O:6][C:4](=[O:5])[C:3]1[C:2]([OH:1])=[CH:13][CH:12]=[CH:11][C:10]=1[O:14][C:21]1[N:22]=[C:23]([O:25][CH3:26])[CH:24]=[C:19]([O:18][CH3:17])[N:20]=1)[CH:8]=[CH2:9]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 22404722HCID 22404722, compound

Product 1

HCID 53901140HCID 53901140, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g of allyl 2,6-dihydroxybenzoate (V) was added to the suspension of 0.4 g of sodium hydride in 50 ml of dimethylformamide and the mixture was stirred for 10 minutes. To this mixture was added 2.2 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine. The reaction mixture was stirred for 5 hours and 50 ml of saturated ammonium chloride solution was added thereto. The reaction solution was then extracted with 200 ml of ethylacetate. The extract was dried over anhydrous sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was subjected to column chromatography (hexane:ethylacetate=2:1 v/v) on silica gel to obtain 3.0 g (Yield 90%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred for 5 hours
  2. extractionThe reaction solution was then extracted with 200 ml of ethylacetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-a3f9da3e9b824052b1ea77b6d1c69bc7
Source dataset
uspto-grants-1996_05
Patent number
US05521146

Reaction notes

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