Pyridine → HCID 19931746, compound

HRID 21440

Reaction equation

HRID 21440 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3][N:2]=1.C([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)=C.N1C=CC=[CH:25][CH:24]=1>>[CH:24]([C:16]1[CH:15]=[CH:14][CH:22]=[CH:21][C:17]=1[C:18]([N:3]1[C:4](=[O:11])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:1]=[N:2]1)=[O:19])=[CH2:25]

Participants

4

Reactant 3

HCID 1049PyridineHCID 110520284-Vinylbenzoyl chlorideHCID 1354087931,2,3-Benzotriazin-4(1H)-one

Product 1

HCID 19931746HCID 19931746, compound

Procedure

A solution of benzo-1,2,3-triazin-4-one (3.8835 g) in dry pyridine (40 mL) was stirred, and to this solution was added, over a period of 30 seconds, freshly prepared 4-vinylbenzoyl chloride (4.3945 g, prepared as described in Hirao et al., Macromolecules, 21, 561 (1988)). The resultant reaction mixture was stirred at room temperature for 1.5 hours, then poured into an ice/water mixture (300 mL). The colorless precipitate which formed was filtered off, washed with water on the frit and dried. The dried product was then dissolved in methylene chloride (75 mL) and the resultant solution was washed with water, dried over anhydrous magnesium sulfate and passed through a short column of silica gel. The solution was then concentrated on a rotary evaporator to give the desired 3-(vinylbenzoyl)benzotriazinone product as a colorless solid (6.12 g) having melting point 120° C. The identity of the product was confirmed by proton nuclear magnetic resonance (NMR) and infra-red spectroscopy, the spectra being as follows:

Workup

  1. additionto this solution was added, over a period of 30 seconds
  2. customThe resultant reaction mixture
  3. customThe colorless precipitate which formed
  4. filtrationwas filtered off
  5. washwashed with water on the frit
  6. customdried
  7. dissolutionThe dried product was then dissolved in methylene chloride (75 mL)
  8. washthe resultant solution was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationThe solution was then concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-64342a59a4714cb6b8cd229ac0523392
Source dataset
uspto-grants-1995_06
Patent number
US05424268

Linked notes

Loading…