Acetone → 4-[5-(Hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]benzene-1-sulfonyl azide

HRID 1462872Notes

Reaction equation

HRID 1462872 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC(C)=O.FC(F)(F)C([O:13][CH2:14][CH:15]1[O:19][C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH2:16]1)=O.C(#N)C>O>[OH:13][CH2:14][CH:15]1[O:19][C:18](=[O:20])[N:17]([C:21]2[CH:22]=[CH:23][C:24]([S:27]([N:1]=[N+:2]=[N-:3])(=[O:28])=[O:29])=[CH:25][CH:26]=2)[CH2:16]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 33557Sodium AzideHCID 20452167HCID 20452167, compound

Product 1

HCID 155913054-[5-(Hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]benzene-1-sulfonyl azide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 10 g sodium azide in 20 ml water was added to 200 ml reagent grade acetone and then cooled to -5° C. A 19 g portion of dl-4-[5-(trifluoroacetoxymethyl)-2-oxooxazolidin-3-yl]benzenesulfonyl chloride (prepared as in Example 1) was added to the solution while maintaining the temperature of the mixture below 0° C. After stirring the mixture for one hour, it was allowed to stand overnight. The acetone was removed under reduced pressure, water was added and the product was filtered and washed with water to yield 12.8 g, m.p. 108°-110° C. This product was stirred with 250 ml acetonitrile at 25° C. and filtered to remove some insoluble material. The acetonitrile was concentrated and the crystallized product filtered to yield 12.3 g. This product was recrystallized from ethyl acetae to yield 6.0 g of the title compound, m.p. 112°-113° C.

Workup

  1. temperaturewhile maintaining the temperature of the mixture below 0° C
  2. waitto stand overnight
  3. customThe acetone was removed under reduced pressure, water
  4. additionwas added
  5. filtrationthe product was filtered
  6. washwashed with water
  7. customto yield 12.8 g, m.p. 108°-110° C
  8. filtrationfiltered
  9. customto remove some insoluble material
  10. concentrationThe acetonitrile was concentrated
  11. filtrationthe crystallized product filtered
  12. customto yield 12.3 g
  13. customThis product was recrystallized from ethyl acetae

Sources & evidence

ORD record
ord-01682e611e584ad19198bc448e7c64f2
Source dataset
uspto-grants-1984_07
Patent number
US04461773

Reaction notes

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