Thionyl Chloride → 4-Chloro-6,7-dimethoxyquinazoline

HRID 717209Notes

Reaction equation

HRID 717209 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=O)[N:7]=[C:6]2[Cl:16].S(Cl)(Cl)=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[Cl:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178486920HCID 178486920, compound

Product 1

HCID 27693644-Chloro-6,7-dimethoxyquinazolineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.12 g (20 mmol) of 6,7-dimethoxy-4-chloro-quinazolinone was placed in a 500 mL single-necked round-bottom flask, and then 120 mL of distilled thionyl chloride containing a drop of DMF was slowly added. The mixture was refluxed. After the completion of the reaction monitored by TLC, the excess amount of thionyl chloride was evaporated under reduced pressure. The residue was dissolved in 300 mL of ethyl acetate, and then washed to neutrality with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate, concentrated, and then purified by column chromatography (Vpetroleum ether:Vethyl acetate=4:1-2:1) to give 6,7-dimethoxy-4-chloro-quinazoline in 85% yield. 1H NMR (DMSO-d6, 400 MHz): 4.01 (s, 6H, 2CH3), 7.38 (s, 1H), 7.45 (s, 1H), 8.88 (s, 1H); ESI-MS (100%): 224 ((M)+, 100).

Workup

  1. temperatureThe mixture was refluxed
  2. customthe excess amount of thionyl chloride was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 300 mL of ethyl acetate
  4. washwashed
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by column chromatography (Vpetroleum ether:Vethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-cb276a03fedc429d9251513ecdde31ac
Source dataset
uspto-grants-2015_11
Patent number
US09193718B2

Reaction notes

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