Acetamidine monohydrochloride → HCID 15087820, compound

HRID 1494645Notes

Reaction equation

HRID 1494645 reaction equation
[C:1]1([N:7]=[N:8][CH:9]([C:13](=O)[CH3:14])[C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:17](=[NH:20])([NH2:19])[CH3:18].[Na]>C(O)C>[CH3:14][C:13]1[C:9]([N:8]=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:10]([CH3:11])[N:20]=[C:17]([NH2:19])[CH:18]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 917853-(Phenylazo)-2,4-pentanedioneHCID 5360545Sodium

Product 1

HCID 15087820HCID 15087820, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 50 parts of 3-(phenylazo)-2,4-pentanedione and 35 parts of ethanimidamide monohydrochloride in 711 parts of ethanol was added a solution of 8.5 parts of sodium in 126 parts of ethanol. After stirring overnight at room temperature, the precipitate was filtered off and the filtrate was stirred for 2 days at room temperature. The mixture was evaporated and the residue was diluted with a sodium hydroxide solution 10%. The separated aqueous layer was extracted with methylbenzene. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated with methylbenzene, yielding 7.5 parts (13.8%) of 4,6-dimethyl-5-(phenylazo)-2-pyridinamine as a residue (int. 95).

Workup

  1. filtrationthe precipitate was filtered off
  2. stirringthe filtrate was stirred for 2 days at room temperature
  3. customThe mixture was evaporated
  4. additionthe residue was diluted with a sodium hydroxide solution 10%
  5. extractionThe separated aqueous layer was extracted with methylbenzene
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated with methylbenzene

Sources & evidence

ORD record
ord-53e47691129b4fd4970e46624c48f1be
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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