Ammonia → HCID 178438078, compound

HRID 2198494Notes

Reaction equation

HRID 2198494 reaction equation
[C:1]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]#[N:9])#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+].N.[N-:17]=[N+:18]=[N-:19].[NH4+]>CN(C)C=O>[NH:2]1[C:1]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]2[NH:19][N:18]=[N:17][N:9]=2)=[N:12][N:11]=[N:10]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 154522,2'-Dicyanodiethyl etherHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 10313046Ammonium azide

Product 1

HCID 178438078HCID 178438078, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

Bis-(2-cyanoethyl)ether 186 g (1.5 mole), 215 g of sodium azide and 177 g of ammonium chloride were slurried in 1070 ml of dimethylformamide. The mixture was heated at 118°-122° C. with stirring and under reflux for 24 hr. (since ammonia and some ammonium azide are evolved, the heating should be done in a hood). After the bulk of the solvent had been removed at 80°-90° C. and 25 mm pressure, the residue was first heated to boiling with 500 ml of water and 40 ml of concentrated hydrochloric acid, then cooled to 5° C. (Caution: some hydrazoic acid is liberated). The product was filtered, washed twice with cold water and dried; 287 g (91%). Recrystallization of 5 g from 85 ml of water furnished coarse blades, m.p. 199°-200° C. (dec.).

Workup

  1. temperatureThe mixture was heated at 118°-122° C.
  2. temperatureunder reflux for 24 hr
  3. customAfter the bulk of the solvent had been removed at 80°-90° C.
  4. temperature25 mm pressure, the residue was first heated
  5. filtrationThe product was filtered
  6. washwashed twice with cold water
  7. customdried
  8. customRecrystallization of 5 g from 85 ml of water
  9. customfurnished coarse blades, m.p. 199°-200° C. (dec.)

Sources & evidence

ORD record
ord-b799fe69e77146658eaf1dd2fb3f7fcc
Source dataset
uspto-grants-1982_11
Patent number
US04358327

Reaction notes

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