Sodium hydride → HCID 14211170, compound

HRID 846239Notes

Reaction equation

HRID 846239 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:18][N:19]([CH3:23])[C:20](Cl)=[S:21]>CN(C)C=O.O>[CH3:18][N:19]([CH3:23])[C:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=1)=[S:21]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 13695066Methyl 4-oxo-4-(4-hydroxyphenyl)butanoate

Product 1

HCID 14211170HCID 14211170, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Step B, 25 g, in anhydrous dimethylformamide (DMF) (300 ml) was cooled to 0° and 99% NaH, 3.46 g, was added in two portions. The mixture was stirred for 1 hour at 0° then dimethylthiocarbamoyl chloride, 19.3 g, was added and the mixture heated at 90° under a N2 atmosphere for 1.5 hours. The mixture was cooled to room temperature and diluted with water to 1,200 mL. The resulting solution was then extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine and then dried over Na2SO4 and evaporated to dryness in vacuo to yield a residue which was purified by chromatography on silica gel to Yield the title compound, mp 62°-64°.

Workup

  1. temperaturethe mixture heated at 90° under a N2 atmosphere for 1.5 hours
  2. extractionThe resulting solution was then extracted with ethyl acetate (3×50 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto yield a residue which
  7. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-852664c0c28745eb871f2f4c1f33cf29
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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