Sodium Nitrate → HCID 58880038, compound

HRID 1642507Notes

Reaction equation

HRID 1642507 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-920324f229744b58a511bf9d20d54886
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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