Isopropanol → HCID 14677481, compound

HRID 1199948Notes

Reaction equation

HRID 1199948 reaction equation
C[N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.Cl.NC1[N:17]=[CH:18][NH:19][C:20]=1[C:21]([NH2:23])=[O:22].C(O)(C)C>C(O)(=O)C>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[N:17]3[CH:18]=[N:19][C:20]([C:21]([NH2:23])=[O:22])=[C:13]3[N:2]=[CH:3][CH:4]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

Product 1

HCID 14677481HCID 14677481, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 17.7 g of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (U.S. Pat. No. 4,281,000, Ex. 1) and 12.6 g of 4-amino-5-imidazolecarboxamide hydrochloride in 100 ml of glacial acetic acid was heated on a steam bath for 4 hours. The reaction mixture was then allowed to stand at room temperature for 16 hours. The mixture was evaporated to dryness in vacuo and the residual solid was partitioned between dichloromethane and saturated sodium bicarbonate. The two layers were separated, the organic layer was dried over anhydrous sodium sulfate and filtered and evaporation of the filtrate gave a dark yellow solid which was treated with isopropyl alcohol. This solid was collected by filtration and washed with hexane. The yellow solid was dried in vacuo to give 10.0 g of the product of the example, mp >260° C.

Workup

  1. customThe mixture was evaporated to dryness in vacuo
  2. customthe residual solid was partitioned between dichloromethane and saturated sodium bicarbonate
  3. customThe two layers were separated
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporation of the filtrate
  7. customgave a dark yellow solid which
  8. filtrationThis solid was collected by filtration
  9. washwashed with hexane
  10. customThe yellow solid was dried in vacuo

Sources & evidence

ORD record
ord-1875e39c8fc04b40a72a6ec72e4e5b4a
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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