Triethylamine → HCID 178418542, compound

HRID 4675

Reaction equation

HRID 4675 reaction equation
[C:1]([C:4](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:5]([CH3:7])=[O:6])(=O)[CH3:2].Cl.[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.C(OCC)(=O)C>C(O)CCC>[C:5]([C:4]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[NH:27][C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:26][C:1]=1[CH3:2])(=[O:6])[CH3:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 80289Benzamidine, hydrochlorideHCID 959903-((3-Nitrophenyl)methylene)-2,4-pentanedione

Product 1

HCID 178418542HCID 178418542, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1-acetyl-1-(3-nitrobenzyliden)acetone (10 g), benzamidine hydrochloride (8.06 g) and triethylamine (8.4 ml) in n-butanol (100 ml) was refluxed for 2 hours. The reaction mixture was added ethyl acetate (100 ml), washed with water (100 ml) and 5% hydrochloric acid (100 ml) successively. The solvent was evaporated and the residue was stirred with ethyl acetate (100 ml) for 1 hour. The crystals were collected by filtration, added a mixture of chloroform (100 ml) and water (100 ml) and adjusted to pH 8.5 by saturated potassium carbonate. The organic layer was evaporated in vacuo to give 5-acetyl-4-methyl-6-(3-nitrophenyl)-2-phenyl-1,6-dihydropyrimidine (4.46 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. washwashed with water (100 ml) and 5% hydrochloric acid (100 ml) successively
  3. customThe solvent was evaporated
  4. filtrationThe crystals were collected by filtration
  5. additionadded
  6. additiona mixture of chloroform (100 ml) and water (100 ml)
  7. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-c3b37e31e5d14c2ab67233d672266e5e
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Linked notes

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