Isatoic Anhydride → HCID 14010425, compound

HRID 1905015Notes

Reaction equation

HRID 1905015 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][NH2:36])[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][N:36]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 14010424HCID 14010424, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 14010425HCID 14010425, compoundYield 99.2%

Procedure

A mixture comprising of 1.63 g 2H-3,1-benzoxazine-2,4-(1H)-dione, 1.78 g of ethyl orthoformate and 2.49 g of 4-(2-ethoxyphenyl)-1-(2-aminoethyl)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. The obtained residue was columnchromatographed over silica gel column and eluted with an ethyl acetate-triethylamine solvent (30:1) to give 3.75 g of 3-[2-[4-(2-ethoxyphenyl)-1-piperazinyl]-ethyl]-4(3H)-quinazolone as an oil (yield: 99.2%).

Workup

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

Sources & evidence

ORD record
ord-91bc55d4c41644c593e33b84a42933e1
Source dataset
uspto-grants-1989_06
Patent number
US04841051

Reaction notes

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