Isatoic Anhydride → HCID 14010430, compound

HRID 1905017Notes

Reaction equation

HRID 1905017 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])O[C:2]1=O.C([O-])([O-])OCC.[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][CH2:36][CH2:37][NH2:38])[CH2:30][CH2:29]1)[CH3:20]>>[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][CH2:36][CH2:37][N:38]2[C:4](=[O:11])[C:5]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:1]=[CH:2]2)[CH2:32][CH2:33]1)[CH3:20]

Participants

4

Reactant 3

HCID 8359Isatoic AnhydrideHCID 20037011HCID 20037011, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 14010430HCID 14010430, compoundYield 66.7%

Procedure

A mixture comprising 1.63 g of 2H-3,1-benzoxazine-2,4(1H)-dione, 1.78 g of ethyl orthoformate and 2.77 g of 4-(2-ethoxyphenyl)-1-(4-aminobutyl)piperazine was heated on a boiling water bath for about 10 minutes and further heated on an oil bath of 120° to 130° C. for about 2 hours. After the completion of the reaction, the reaction mixture was concentrated under a reduced pressure and the residue was columnchromatographed over silica gel column and eluted with an ethyl acetatetriethylamine solvent (30:1) to give 1.5 g of 3-{4-[4-(2-ethoxyphenyl)-1-piperazinyl]butyl}-4(3H)-quinazolone as an oil (yield: 66.7%). ##STR15## 1.50 g of this oily free base was dissolved in a small amount of acetone. The obtained solution was added to a saturated solution of 0.857 g of fumaric acid in acetone to precipitate a crude crystal. The crude crystal was recrystallized from ethanol to give 1.65 g of the corresponding monofumarate having a melting point of 197° to 198° C. as a colorless prisms.

Workup

  1. temperaturewas heated on a boiling water bath for about 10 minutes
  2. temperaturefurther heated on an oil bath of 120° to 130° C. for about 2 hours
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated under a reduced pressure
  5. washeluted with an ethyl acetatetriethylamine solvent (30:1)

Sources & evidence

ORD record
ord-e4083833fb17469382f177f862b8e99d
Source dataset
uspto-grants-1989_06
Patent number
US04841051

Reaction notes

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