Sodium Nitrite → HCID 66831721, compound

HRID 570936Notes

Reaction equation

HRID 570936 reaction equation
[CH3:1][S:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14](N)=[O:15])=[C:7]2[N:6]=[N:5]1.N([O-])=[O:18].[Na+]>C(O)(C(F)(F)F)=O.O>[CH3:1][S:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14]([OH:15])=[O:18])=[C:7]2[N:6]=[N:5]1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 44128652HCID 44128652, compound

Product 1

HCID 66831721HCID 66831721, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3-(methylthiomethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (12.43 mmol, 3 g, 1 eq.) in TFA (12 mL) was added sodium nitrite (43.5 mmol, 3 g, 3.5 eq.) dissolved in water (6 mL) portion-wise keeping exothermic effervescence under control and the mixture was stirred at room temperature for over 3 hours. The reaction mixture was poured into ice and it was gently stirred until the ice melted. The resulted suspension was filtered, washed with water and ether and dried under vacuum to give the title compound. Yield=61%. δH (DMSO-d6) 8.85 (1H, s), 5.44 (2H, s), 2.25 (3H, s).

Workup

  1. additionThe reaction mixture was poured into ice and it
  2. filtrationThe resulted suspension was filtered
  3. washwashed with water and ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c416670a4f864a3ca750b68679468eaf
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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