Dichloromethane → HCID 90411683, compound

HRID 717362Notes

Reaction equation

HRID 717362 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])[N:9]=[C:8]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)[N:7]=[C:6]2O.[Cl:28]CCl.C(Cl)(C(Cl)=O)=O>CN(C=O)C>[Cl:28][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[C:8]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 178486783HCID 178486783, compound

Product 1

HCID 90411683HCID 90411683, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

Into a 1-L 3-necked round-bottom flask, was placed 6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazolin-4-ol (12 g, 32.23 mmol, 1.00 equiv), dichloromethane (400 mL) and DMF (cat.) (0.1 g). This was followed by the addition of (COCl)2 (40 g, 315.21 mmol, 9.78 equiv) dropwise with stirring at 0-10° C. The resulting solution was heated to reflux for 5 h. The mixture was cooled to room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was dissolved in 400 mL of dichloromethane. The resulting mixture was washed with 2×200 mL of NaHCO3 (sat.) and 1×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/ethyl acetate (2:1). This resulted in 5 g (40%) of 4-chloro-6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline as a yellow solid. MS (ESI) m/z 391 [M+H]+

Workup

  1. customInto a 1-L 3-necked round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 h
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. dissolutionThe residue was dissolved in 400 mL of dichloromethane
  8. washThe resulting mixture was washed with 2×200 mL of NaHCO3 (sat.) and 1×200 mL of brine
  9. dry with materialThe mixture was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under vacuum
  11. customThis resulted in 5 g (40%) of 4-chloro-6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)quinazoline as a yellow solid

Sources & evidence

ORD record
ord-ddc629c2a2c04fc4bc844803c2f702bd
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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