Sodium Azide → HCID 178527918, compound

HRID 1588185Notes

Reaction equation

HRID 1588185 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]=[C:10]=[S:11])[CH2:3][CH2:2]1.[N-:12]=[N+:13]=[N-:14].[Na+]>C(O)C.O>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][N:9]2[C:10](=[S:11])[NH:14][N:13]=[N:12]2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 1439572-Morpholinoethyl isothiocyanate

Product 1

HCID 178527918HCID 178527918, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a mechanically stirred slurry of 25.8 g (0.15 mole) of 2-morpholinoethylisothiocyanate (S-7) in 250 ml ethanol under a nitrogen atmosphere was added in a slow stream 19.5 g (0.3 mole) of sodium azide dissolved in 600 ml water. The resultant solution was refluxed for 16 hrs, cooled to room temperature (20° C.) and filtered. The filtrate was extracted twice with ether, and then acidified to pH=1 with concentrated hydrochloric acid. The resultant solution was extracted three times with ether. The pH of the aqueous solution was adjusted to 4.5 using a 50% NaOH solution and a fine white precipitate formed. The precipitate was collected by filtration to yield 17.1 grams of intermediate S-8 with a melting point of 226°-8° C.

Workup

  1. filtrationfiltered
  2. extractionThe filtrate was extracted twice with ether
  3. extractionThe resultant solution was extracted three times with ether
  4. customa fine white precipitate formed
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-aaa6f3aa31a54cb782c8feb6bac07d3d
Source dataset
uspto-grants-1993_06
Patent number
US05221600

Reaction notes

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