Ammonium Hydroxide → HCID 178510969, compound

HRID 2109974Notes

Reaction equation

HRID 2109974 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[N:12].C([O:15][C:16]([N:18]=[C:19]=[S:20])=O)C.[OH-].[NH4+]>CCOC(C)=O>[OH:15][C:16]1[N:6]2[N:5]=[CH:4][C:3]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[C:2]2[N:1]=[C:19]([SH:20])[N:18]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 85320Ethyl isothiocyanatoformateHCID 57635950HCID 57635950, compound

Product 1

HCID 178510969HCID 178510969, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound (2) (4.6 g. 14 mmol) in EtOAc (50 mL) was added Ethoxycarbonyli-sothiocyanate (1.69 mL, 15 mmol) drop wise with stirring at ambient temperature. The reaction mixture was refluxed for 2 h, and cooled to room temperature. Ammonium hydroxide (10 mL) was added and the reaction mixture stirred at room temperature for 20 h. The reaction mixture was extracted twice with 1 M NaOH and the aqueous extractions were combined, acidified with concentrate HCl, and extracted twice with EtOAc. The combined organic extracts were dried with anhydrous Na2SO4 and concentrated to give 5-(4-hydroxy-2-mercapto-pyrazolo[1,5-a][1,3,5]triazin-8-yl)-pentanenitrile (3), as a white solid (2.5 g, 67%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperaturecooled to room temperature
  3. stirringthe reaction mixture stirred at room temperature for 20 h
  4. extractionThe reaction mixture was extracted twice with 1 M NaOH
  5. extractionthe aqueous extractions
  6. extractionextracted twice with EtOAc
  7. dry with materialThe combined organic extracts were dried with anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bd0c4f33792c47d2aca032f171434ba4
Source dataset
uspto-grants-2009_04
Patent number
US07517882B2

Reaction notes

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