p-Toluenesulfonic acid monohydrate → HCID 15583183, compound

HRID 2418213Notes

Reaction equation

HRID 2418213 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[NH:15][NH:16][C:17](=O)[CH2:18][CH2:19][Cl:20])[CH:2]=[CH2:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[C:17]([CH2:18][CH2:19][Cl:20])=[N:16][N:15]=[C:5]12)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 15583182HCID 15583182, compound

Product 1

HCID 15583183HCID 15583183, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.30 g of 3-allyl-2-[2-(3-chloropropionyl)hydrazino]quinazolin-4(3H)-one (0.0173 mol) and 10 mg of p-toluenesulfonic acid hydrate in 300 ml of ethanol was refluxed for 17 hours until TLC indicated that no starting material remained. The mixture was evaporated to dryness and the remaining yellow oil was dissolved in dichloromethane. The solution was washed twice with water, dried over MgSO4, filtered and evaporated. The resulting solid was purified by column chromatography using Kieselgel 60 with CH2Cl2 +1% MeOH as eluant and then was finally crystallized from ethanol to obtain 2.625 g (53% yield) of 4-allyl-1-(2-chloroethyl)[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one melting at 142.5°-144° C.

Workup

  1. temperaturewas refluxed for 17 hours until TLC
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe remaining yellow oil was dissolved in dichloromethane
  4. washThe solution was washed twice with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid was purified by column chromatography
  9. customwas finally crystallized from ethanol

Sources & evidence

ORD record
ord-26cf7cee479f4be1a7c7eae72660b9dd
Source dataset
uspto-grants-1984_09
Patent number
US04472400

Reaction notes

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