Oxalyl chloride → 4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

HRID 1869109Notes

Reaction equation

HRID 1869109 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[NH:12][C:11](=O)[N:10]=[CH:9]2.C(Cl)(=O)C([Cl:25])=O>C(Cl)(Cl)Cl.CN(C=O)C>[Cl:25][C:9]1[C:8]2[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 18925053HCID 18925053, compound

Product 1

HCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazolineYield 97.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

To 6,7-bis(2-methoxy-ethoxy)-quinazolone (500 mg, 1.7 mmol), from Preparation 1, in CHCl3 (10 mL) containing one drop of DMF was added oxalylchloride (490 μL, 5.6 mmol) in several portions over 5 minutes. Once foaming ceased the solution was refluxed 1.5 hours. The solvent was removed in vacuo and the residue was dissolved in 1,2-dichloroethane (20 mL) and washed two times with 80 mL saturated aqueous Na2CO3. The organic phase was dried over Na2SO4, and concentrated in vacuo to afford solid title product (520 mg, 92%; M.P. 108°-109° C.).

Workup

  1. temperaturewas refluxed 1.5 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 1,2-dichloroethane (20 mL)
  4. washwashed two times with 80 mL saturated aqueous Na2CO3
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c803862932644431bd0f0d60a2aea459
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

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