Nitric Acid → HCID 54573928, compound

HRID 2419148Notes

Reaction equation

HRID 2419148 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([CH:5]([OH:23])[C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[C@@H:7]1[OH:22])=[O:4].OS(O)(=O)=O.O=S(=O)=O.[N+:34](C)([O-:36])=[O:35].C(=O)(O)[O-].[K+].[N+:43]([O-])([OH:45])=[O:44]>O>[CH3:1][N:2]([CH3:24])[C:3]([CH:5]([OH:23])[C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([O:21][N+:34]([O-:36])=[O:35])[C@@H:7]1[O:22][N+:43]([O-:45])=[O:44])=[O:4]

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 6375NitromethaneHCID 24681Fuming sulfuric acidHCID 516893Potassium BicarbonateHCID 53838578HCID 53838578, compound

Product 1

HCID 54573928HCID 54573928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.16 g of adenosine-5'-carboxylic acid dimethylamide were dissolved at -40° C in 60 ml of fuming nitric acid (d = 1.50). A mixture, cooled to -20° C, of 30 ml of oleum and 30 ml of nitromethane was added dropwise to this solution within 30 minutes at such a rate that the temperature did not rise above -30° C. The mixture was stirred for 45 minutes at a temperature between -30° C and -25° C and then poured on to a solution of 325 g of potassium bicarbonate in 1 liter of water. By extraction with chloroform or with chloroform containing 5% n-propanol, there was obtained practically pure 2',3'-di-O-nitroadenosine-5'-carboxylic acid dimethylamide which melted at 156.5° C (decomposition) after recrystallisation from alcohol. The yield was 5.78 g (72.7% of theory).

Workup

  1. additionwas added dropwise to this solution within 30 minutes at such a rate that the temperature
  2. customdid not rise above -30° C
  3. extractionBy extraction with chloroform

Sources & evidence

ORD record
ord-3cc00b108c324e54b1f23f8ec442c273
Source dataset
uspto-grants-1978_08
Patent number
US04104462

Reaction notes

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