Sodium Iodide → HCID 14456867, compound

HRID 279781Notes

Reaction equation

HRID 279781 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH:9]([CH2:10]OS(C)(=O)=O)[CH2:8][C:7]1=[O:16].[I-:23].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH:9]([CH2:10][I:23])[CH2:8][C:7]1=[O:16]

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 13505934HCID 13505934, compound

Product 1

HCID 14456867HCID 14456867, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 37.5 g (0.107 mole) of 1-(2,4-dimethoxy-benzyl)-4-(mesyloxymethyl)-2-azetidinone prepared according to the preceding paragraph, 250 ml of anhydrous acetone, and 56.3 g (0.376 mole) of sodium iodide is heated to boiling for 8 hours. To the mixture a further amount of 18.8 g (0.125 mole) of sodium iodide are added and the mixture is stirred for a further 8 hours under boiling. The mixture is evaporated to dryness on a water-bath (internal temperature 50° C.), the residue is rubbed with 100 ml of water and the oil thus obtained is extracted with 100 ml of dichloromethane. The aqueous layer is extracted three times with 50 ml of dichloromethane each. The united dichloromethane layers are dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated. Thus 40.3 g of 1-(2,4-dimethoxy-benzyl)-4-(iodomethyl)-2-azetidinone are obtained. Yield: 98%.

Workup

  1. customprepared
  2. temperatureis heated
  3. customThe mixture is evaporated to dryness on a water-bath (internal temperature 50° C.)
  4. customthe oil thus obtained
  5. extractionis extracted with 100 ml of dichloromethane
  6. extractionThe aqueous layer is extracted three times with 50 ml of dichloromethane each
  7. dry with materialThe united dichloromethane layers are dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-b4e36deae4a942f78db7fcfcdd295c3f
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

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