Hydrazine hydrate (1:1) → 5-amino-3-(morpholin-4-yl)-1H-pyrazole-4-carbonitrile

HRID 1068889Notes

Reaction equation

HRID 1068889 reaction equation
O.[NH2:2][NH2:3].[N:4]1([C:10](SC)=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1>CO>[NH2:13][C:12]1[NH:3][N:2]=[C:10]([N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[C:11]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17044482-[(Methylsulfanyl)(morpholin-4-yl)methylidene]propanedinitrile

Product 1

HCID 49626575-amino-3-(morpholin-4-yl)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.78 ml (56 mmol) of hydrazine hydrate are added to a slurry of 9.8 9 (46.8 mmol) of 3-(morpholin-4-yl)-3methylsulfanyl-2-cyanoacrylonitrile in 60 ml of methanol and heated to boiling, with the solid dissolving. After 3.5 hours, the reaction mixture is cooled to RT, concentrated by evaporation and recrystallised from ≈70 ml of boiling ethanol, yielding 5-amino-3-(morpholin-4-yl)-1H-pyrazole-4-carbonitrile: m.p. 199-201° C.; TLC: Rf=0.19 (ethyl acetate/toluene=3 3:1).

Workup

  1. temperatureheated
  2. dissolutiondissolving
  3. concentrationconcentrated by evaporation
  4. customrecrystallised from ≈70 ml of boiling ethanol

Sources & evidence

ORD record
ord-7ed249ad45194310ad30ee2bd2aeb335
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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