Acetic Acid → 3-Nitroso-2-phenylimidazo(1,2-a)pyrimidine
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[N:14]=[CH:13][CH:12]=[CH:11][N:10]3[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[N:20]([O-])=[O:21].[Na+]>O>[N:20]([C:15]1[N:10]2[CH:11]=[CH:12][CH:13]=[N:14][C:9]2=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A mixture of 20 g of 2-phenylimidazo(1,2-a)pyrimidine, 200 ml of glacial acetic acid and 20 ml of water is warmed with stirring until the solids are completely dissolved. The solution is next cooled to 5° C. in an ice/salt bath. A solution of 15 g of NaNO2 in 50 ml of water is added dropwise to the cooled acetic acid solution while the solution is kept between 0°-5° C. throughout the addition of NaNO2 solution and three hours thereafter. The reaction mixture is further stirred for 12 more hours at room temperature. The green precipitate is filtered and washed thoroughly with water on a glass filter. The residue is recrystallized once from 2-propanol to yield about 15 g of 3-nitroso-2-phenylimidazo(1,2-a)pyrimidine, m.p. 223°-225° C.
Workup
- temperatureis warmed
- dissolutionare completely dissolved
- stirringThe reaction mixture is further stirred for 12 more hours at room temperature
- filtrationThe green precipitate is filtered
- washwashed thoroughly with water on a glass
- filtrationfilter
- customThe residue is recrystallized once from 2-propanol
Sources & evidence
- ORD record
- ord-b35b682adcb14faf862dbf5b083f2d5b
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255573
Reaction notes
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