Sodium Nitrate → HCID 58880038, compound

HRID 1882197Notes

Reaction equation

HRID 1882197 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[N+:16]([O-])([O-])=O.[Na+]>C(O)(=O)C.O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:14]3[N:15]=[N:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 24268Sodium Nitrate2×HCID 28846343HCID 28846343, compound

Product 1

HCID 58880038HCID 58880038, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 2 (3.8 g, 14.4 mmol) was dissolved in a mixture of acetic acid (4 ml), water (4 ml) and methylene chloride (4 ml). The mixture was cooled to 0° C., then sodium nitrate (1.29 g, 18.7 mmol) was slowly added. Upon completion of the addition of sodium nitrate, the mixture was brought to room temperature and stirred for 20 minutes. The intended product was confirmed by LC-MS. Methylene chloride (30 ml) was added to the solution and the solution was then washed with water (3×30 ml). The organic layer was dried over magnesium sulfate and then evaporated to provide the title compound (2.9 g, 73%). [M+H] calc'd for C11H7BrN4, 274; found, 274.

Workup

  1. customwas brought to room temperature
  2. washthe solution was then washed with water (3×30 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-3753415218e540a7be4ed7991b461f25
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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