Ammonia → HCID 21187097, compound

HRID 1384500Notes

Reaction equation

HRID 1384500 reaction equation
[NH3:1].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=[C:10]=[S:11])#[N:3]>O1CCOCC1>[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH2:1])=[S:11])#[N:3]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 21187095HCID 21187095, compound

Product 1

HCID 21187097HCID 21187097, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a 0.5M solution of ammonia in dioxane (80 ml) at 10° C. was added 5-cyanopentyl isothiocyanate (5 g) and the solution was stirred at room temperature overnight. TLC of the reaction mixture still showed the presence of some starting material. Additional ammonia in dioxane (40 ml) was added and the solution was stirred for a further 6 hours. At this stage, the reaction was found to be complete as judged by TLC analysis. The solvent was then removed on a rotary evaporator and to the residue was added methyl tert-butyl ether (40 ml). The mixture was then heated on steam bath briefly (the solid did not dissolve) then cooled to give the required product as a colorless crystalline material (5 g), m.p. 69-71° C.

Workup

  1. stirringthe solution was stirred for a further 6 hours
  2. customThe solvent was then removed on a rotary evaporator and to the residue
  3. additionwas added methyl tert-butyl ether (40 ml)
  4. temperatureThe mixture was then heated on steam bath briefly (the solid
  5. dissolutiondid not dissolve)
  6. temperaturethen cooled

Sources & evidence

ORD record
ord-ae81c9797a094ebdb55a2fa47b08f79e
Source dataset
uspto-grants-2001_07
Patent number
US06258976B1

Reaction notes

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