Potassium Hydroxide → HCID 86736887, compound

HRID 1701507Notes

Reaction equation

HRID 1701507 reaction equation
[CH:1]1[N:6]=[C:5]2[C:7]([NH:9][C:10](=O)[C:4]2=[N:3][CH:2]=1)=O.[OH-].[K+].CS(O)(=O)=O.O[CH2:20][CH2:21][N:22]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][N:24]=[C:23]1[CH3:30].OCCN1C([N+]([O-])=O)=CNC1(C)CS([O-])(=O)=O>CN(C)C=O.CO>[CH3:30][C:23]1[N:22]([CH2:21][CH2:20][N:9]2[CH2:7][C:5]3[C:4](=[N:3][CH:2]=[CH:1][N:6]=3)[CH2:10]2)[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][N:24]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 1345822,3-Pyrazinedicarboximide (8CI)HCID 21491666HCID 21491666, compoundHCID 86736888HCID 86736888, compound

Product 1

HCID 86736887HCID 86736887, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 1.80 parts by weight of 2,3-pyrazinedicarboximide which was prepared according to the procedure described in Helvetica Chemica Acta 41 (1958) p. 512 in 40 parts by volume of dry dimethylformamide is added 17.0 parts by volume of methanol containing 0.85 parts by weight of potassium hydroxide pellets. The combination of these two solutions results in the formation of a precipitate. To this mixture is then added in one portion a slightly warm solution of 3.01 parts by weight of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole methanesulfonate (preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazolemethanesulfonate is described in U.S. Pat. No. 3,770,763) in 40.0 parts by volume of dimethylformamide. The mixture turns dark blue in color, then upon swirling turns green in color and eventually turns yellow in color. The mixture is then heated on a steam bath for 4 hours at an internal temperature of 70°-85° C. After cooling, the mixture to room temperature the insoluble material is separated by filtration, rinsed with dimethylformamide and air dried. The mother liquor is rinsed into a round bottom flask, concentrated to a volume of about 40 parts, then diluted to a volume of 100 parts with water and allowed to stand overnight. The resulting solid material which separates out of this liquor is separated by filtration, washed with water and air dried to afford a product, in the form of brown needles, melting at 231°-234° C. This product is then taken up in 8.0 parts by volume of warm dimethylformamide; activated carbon is added to the solution and the solution is then filtered. The filtrate is diluted with 20 parts by volume of water and then seeded. The resulting crystals are separated by filtration, washed with methanol and air dried to afford 6-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethyl]-5H-pyrrolo[3,4-b]pyrazine-5,7(6H-dione), melting at 232°-234° C. This compound is represented by the following structural formula ##STR7##

Workup

  1. customThe combination of these two solutions results in the formation of a precipitate
  2. temperatureThe mixture is then heated on a steam bath for 4 hours at an internal temperature of 70°-85° C
  3. temperatureAfter cooling
  4. customthe mixture to room temperature the insoluble material is separated by filtration
  5. washrinsed with dimethylformamide and air
  6. customdried
  7. washThe mother liquor is rinsed into a round bottom flask
  8. concentrationconcentrated to a volume of about 40 parts
  9. additiondiluted to a volume of 100 parts with water
  10. customis separated by filtration
  11. washwashed with water and air
  12. customdried
  13. customto afford a product
  14. additionactivated carbon is added to the solution
  15. filtrationthe solution is then filtered
  16. additionThe filtrate is diluted with 20 parts by volume of water
  17. customThe resulting crystals are separated by filtration
  18. washwashed with methanol and air
  19. customdried

Sources & evidence

ORD record
ord-4db2215b3531492d8e15a2eec1d41e84
Source dataset
uspto-grants-1980_03
Patent number
US04193979

Reaction notes

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