Dimethylformamide → HCID 67819964, compound

HRID 1033055Notes

Reaction equation

HRID 1033055 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([OH:25])(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[N+:19]([O-])[CH:18]=1.[NH2:26][CH2:27][C:28]1[O:32][C:31]([C:33]2[N:34]=[C:35]([N:38]=[C:39]([NH2:41])[NH2:40])[S:36][CH:37]=2)=[CH:30][CH:29]=1.CN(C)C=[O:45]>>[NH2:40][C:39](=[N:38][C:35]1[S:36][CH:37]=[C:33]([C:31]2[O:32][C:28]([C:27]([NH:26][C:16](=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=3)=[O:45])=[CH:29][CH:30]=2)[N:34]=1)[NH2:41]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 16976Oxiniacic AcidHCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 67819964HCID 67819964, compound

Procedure

Dicyclohexylcarbodiimide (2.3 g) was added slowly to a suspension of nicotinic acid N-oxide (1.5 g) in N,N-dimethylformamide (40 ml) with cooling on an ice bath and the mixture was stirred for 15 minutes with cooling on an ice bath. To the mixture 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (2.0 g) was added with cooling on an ice bath. The mixture was stirred for an hour with cooling on an ice bath and then stirred for 41 hours at room temperature. The solvent was removed under reduced pressure and the residue was suspended in water. 6N-Hydrochloric acid solution was added to the suspension and the resulting precipitate was removed by filtration. The solvent was removed under reduced pressure and the residue was dissolved in methanol. The insoluble material was removed by filtration and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (10:1, V/V). Recrystallization from a mixture of methanol, dioxane and diisopropyl ether afforded 2-(diaminomethyleneamino)-4-[5-(1-oxonicotinoylaminomethyl)furan-2-yl]thiazole (0.30 g).

Workup

  1. temperaturewith cooling on an ice bath
  2. temperaturewith cooling on an ice bath
  3. temperaturewith cooling on an ice bath
  4. stirringThe mixture was stirred for an hour
  5. temperaturewith cooling on an ice bath
  6. stirringstirred for 41 hours at room temperature
  7. customThe solvent was removed under reduced pressure
  8. addition6N-Hydrochloric acid solution was added to the suspension
  9. customthe resulting precipitate was removed by filtration
  10. customThe solvent was removed under reduced pressure
  11. dissolutionthe residue was dissolved in methanol
  12. customThe insoluble material was removed by filtration
  13. customthe solvent was removed under reduced pressure
  14. customThe residue was chromatographed on a silica gel column
  15. washeluting with a mixture of chloroform and methanol (10:1, V/V)
  16. customRecrystallization
  17. additionfrom a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-0bf211e9da8d48c59caba4ff55c97ab4
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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