Sodium Azide → HCID 21394064, compound

HRID 460745Notes

Reaction equation

HRID 460745 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][CH2:7][CH2:8][C:9]1([CH3:16])[NH:13][C:12](=[O:14])[NH:11][C:10]1=[O:15].[N-]=[N+]=[N-]>O.CN(C)C=O>[N:1]([CH2:6][CH2:7][CH2:8][C:9]1([CH3:16])[NH:13][C:12](=[O:14])[NH:11][C:10]1=[O:15])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 33558AzideHCID 21394062HCID 21394062, compound

Product 1

HCID 21394064HCID 21394064, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of sodium azide (13 g, 0.2 mol) in water (100 ml) was added to a solution of 5-(3-chloropropyl)-5-methyl-2,4-imidazolidinedione (19.06 g, 0.1 mol) in dimethylformamide (900 ml.) and the mixture was kept at 75° C. for 21 hours. Iodometric determinations of azide ions indicated the consumption of the expected quantities of azide at that time. The mixture was concentrated to a syrup which was redissolved in chloroform (200 ml.), filtered, diluted with chloroform (500 ml.) and water (100 ml.), the chloroform phase was collected after equilibration and combined with four additional chloroform extracts which were dried (MgSO4) and concentrated. Crystalline 5-(3-azidopropyl)-5-methyl-2,4-imidazolidinedione was obtained from chloroform/petroleum ether (17.3 g, 88%), m.p. 104° C. after one recrystallization from the same solvent.

Workup

  1. customthe consumption of the expected quantities of azide at that time
  2. concentrationThe mixture was concentrated to a syrup which
  3. dissolutionwas redissolved in chloroform (200 ml.)
  4. filtrationfiltered
  5. additiondiluted with chloroform (500 ml.) and water (100 ml.)
  6. customthe chloroform phase was collected after equilibration
  7. dry with materialwere dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-38d62fe50a474d89add0d986fa0dab48
Source dataset
uspto-grants-1977_12
Patent number
US04061542

Reaction notes

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