Acetonitrile → HCID 14677477, compound

HRID 1199947Notes

Reaction equation

HRID 1199947 reaction equation
C[N:2]([CH3:15])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=O.Cl.NC1[N:19]=[CH:20][NH:21][C:22]=1[C:23]([NH2:25])=[O:24].C(=O)(O)[O-].[Na+].C(#N)C>C(O)(=O)C>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:19]3[CH:20]=[N:21][C:22]([C:23]([NH2:25])=[O:24])=[C:15]3[N:2]=[CH:3][CH:4]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 7224023-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one

Product 1

HCID 14677477HCID 14677477, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 15.0 g of 3-dimethylamino-4'-methoxyacrylophenone (prepared as described in Example 8) and 9.2 g of 4-amino-5-imidazolecarboxamide hydrochloride in 450 ml of glacial acetic acid was heated at reflux for 24 hours. Evaporation of the solvent in vacuo gave a solid which was treated with saturated sodium bicarbonate solution, then washed with water and filtered to give colorless crystals. This material was treated with hot acetonitrile and collected by filtration. Recrystallization from ethanol gave 6.1 g of the desired product as yellow crystals, mp 246°-249° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customEvaporation of the solvent in vacuo
  4. customgave a solid which
  5. washwashed with water
  6. filtrationfiltered
  7. customto give colorless crystals
  8. filtrationcollected by filtration
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-c21cfe32d8c9452794321249b8715fa2
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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