Dichloromethane → HCID 45119990, compound

HRID 1419856Notes

Reaction equation

HRID 1419856 reaction equation
[OH-].[Na+].[CH2:3](Cl)Cl.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:17](=[O:18])[C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)=[C:15]([NH2:26])[O:14]1.S(OC)(OC)(=O)=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:17](=[O:18])[C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)=[C:15]([NH:26][CH3:3])[O:14]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 70197198HCID 70197198, compound

Product 1

HCID 45119990HCID 45119990, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Solid sodium hydroxide(180 mg, 4.50 mmol) was dissolved in a small amount of water and then added to methylene chloride (8.6 ml) containing 2-(o-chlorophenyl)-3-oxo-4-(4-methylpyridyl)-5-amino-2,3-dihydrofuran(400 mg, 1.3 mmol). Tetrabutylammonium bromide (50.0 mg, 1.37 mmol) was added and then a mixture containing dimethyl sulfate (164 mg, 1.30 mmol) was slowly added at room temperature. The mixture was stirred at room temperature for one hour and then washed twice with water, dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to yield a crude product, which was separated by column-chromatography over silica gel to obtain the desired product (370 mg, yield=88%) as a white solid.

Workup

  1. additionwas slowly added at room temperature
  2. washwashed twice with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customto yield a crude product, which
  6. customwas separated by column-chromatography over silica gel

Sources & evidence

ORD record
ord-5d716ce897b04124bd79547a7d4d0f6f
Source dataset
uspto-grants-1999_03
Patent number
US05889027

Reaction notes

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