Triethylamine → HCID 178466934, compound

HRID 255703Notes

Reaction equation

HRID 255703 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]=[CH:7][C:8]([CH2:10]C(=O)C)=[O:9])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].Cl.[C:20]([NH2:28])(=[NH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:29](N(CC)CC)[CH3:30].C(OCC)(=O)C>C(O)CCC>[C:8]([C:7]1[CH:6]([C:5]2[CH:14]=[CH:15][C:2]([OH:1])=[C:3]([N+:16]([O-:18])=[O:17])[CH:4]=2)[NH:28][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:27][C:29]=1[CH3:30])(=[O:9])[CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 80289Benzamidine, hydrochlorideHCID 570301622-(4-Hydroxy-3-nitrobenzylidene)acetylacetone

Product 1

HCID 178466934HCID 178466934, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-(4-hydroxy-3-nitrobenzylidene)acetylacetone (40 g), benzamidine hydrochloride (30.2 g) and triethylamine (31.2 ml) in n-butanol (400 ml) was refluxed for 2 hours. The reaction mixture, added ethyl acetate (100 ml), was washed with water (200 ml) and 5% hydrochloric acid (200 ml) successively. The solvent was evaporated and the residue was stirred with ethyl acetate (200 ml) for 1 hour. The crystals were collected by filtration, added a mixture of chloroform (200 ml) and water (200 ml) and adjusted to pH 8.5 by saturated potassium carbonate. The organic layer was evaporated in vacuo to give crude 5-acetyl-1,6-dihydro-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-phenylpyrmidine (45.5 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. washwas washed with water (200 ml) and 5% hydrochloric acid (200 ml) successively
  3. customThe solvent was evaporated
  4. filtrationThe crystals were collected by filtration
  5. additionadded
  6. additiona mixture of chloroform (200 ml) and water (200 ml)
  7. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-fc6db7eb11c4472c8e926d4e8c83ff7a
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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